Tag: M.W:300-400

170147-29-2, tert-Butyl 5-(benzyloxy)-1H-indole-1-carboxylate is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of scheme 6-6 compound S2 (2 g, 6.19 mmol) in MeCN (40 mL) at 0 C was added chlorosulfonyl isocyanate dropwise (0.57 mL, 6.50 mol). The reaction was stirred at room temperature overnight and then acetone (40 mL) and H20 (5 mL) was added followed by dropwise addition of 10% aq.KOH solution (2 mL). The mixture was stirred at room temperature for 30 mm and extracted with ethyl acetate (50 mL x 2). The combined organic phases were washed with brine, dried over anhydrous Na2SO4, filtered and concentrated to dryness. The residue was further washed with EtOAc to give the title compound (1.7 g, 75% yield) as a white solid. LC/MS (ESI) m/z: 311 (M-56+H) +, 170147-29-2

170147-29-2 tert-Butyl 5-(benzyloxy)-1H-indole-1-carboxylate 10663688, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; ACHILLION PHARMACEUTICALS, INC.; WILES, Jason Allan; PHADKE, Avinash S.; DESHPANDE, Milind; AGARWAL, Atul; CHEN, Dawei; GADHACHANDA, Venkat Rao; HASHIMOTO, Akihiro; PAIS, Godwin; WANG, Qiuping; WANG, Xiangzhu; GREENLEE, William; (358 pag.)WO2017/35411; (2017); A1;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1265231-91-1,3-(Dimethylamino)-2-(1-(phenylsulfonyl)-1H-indole-2-carbonyl)acrylonitrile,as a common compound, the synthetic route is as follows.

Methyl 5-hydrazinyl-1H-benzo[d]imidazole-2-carboxylatedihydrochloride 2e (300mg, 1.07mmol) and 3-(dimethylamino)-2-(1-(phenylsulfonyl)-1H-indole-2-carbonyl)acrylonitrile If (408mg, 1.07mmol) were suspended in 30mL of absolute ethanol and the reaction solution was refluxed for 6 hours. The solution was subjected to suction filtration, the filter cake was washed with 5mL of ethanol, and the filtrate was concentrated under reduced pressure. The residue was further separated and purified by silica gel column chromatography (developing agent: system B) to obtain methyl 5-(5-amino-4-(1-(phenylsulfonyl)-1H-indole-2-carbonyl)-1H-pyrazol-1-yl)-1H-benzo[d]imidazol -2-carboxylate 2g (143mg, yellow solid), yield: 24%. MS m / z (ESI): 540.7 [M + 1]

1265231-91-1, As the paragraph descriping shows that 1265231-91-1 is playing an increasingly important role.

Reference：
Patent; Zhejiang Hisun Pharmaceutical Co., Ltd; CHEN, Lei; GUAN, Dongliang; BAI, Hua; YAN, Xing; MIAO, Shuai; ZHU, Songsong; (54 pag.)EP3339305; (2018); A1;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

1059630-08-8, (4aS,9bR)-Ethyl 6-bromo-3,4,4a,5-tetrahydro-1H-pyrido[4,3-b]indole-2(9bH)-carboxylate is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 1 : To a degassed mixture of (4aS,9bR)-ethyl 6-bromo-3,4,4a,5-tetrahydro- lH-pyrido[4,3-b]indole-2(9bH)-carboxylate (1.60 g, 8.0 mmol), 2-chloro-2,2-di- deuteri oacetam i de (2.5 g, 26 mmol), and KI (2.68 g, l6mmol) in dioxane (30 mL), diisopropylethylamine (3.0 mL, 16 mmol) is added at room temperature. The reaction mixture is then heated to 104 C under vigorous stirring for 5 days. Solvents are removed under vacuum and the residue is suspended in dichloromethane (50 mL) and extracted with water (20 mL). The organic phase is separated, dried over anhydrous K2CO3 and (0280) concentrated to a residue. The product is purified by silica gel column chromatography using a gradient of 0 – 100% ethyl acetate in hexanes to obtain (4aS,9bR)-ethyl 5-(2-amino- 1 , 1 -di- 2-oxoethyl)-6-bromo-3,4,4a,5-tetrahydro-lH-pyrido[4,3-b]indole-2(9bH)-carboxylate as a brown oil (1.26 g, yield 41%). MS (ESI) m/z 384.1 [M+l]. The synthesis of the starting material is disclosed in US 2010/113781. The reaction scheme is shown below:

1059630-08-8, The synthetic route of 1059630-08-8 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; INTRA-CELLULAR THERAPIES, INC.; LI, Peng; ZHANG, Qiang; DAVIS, Robert; (63 pag.)WO2019/183341; (2019); A1;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.170147-29-2,tert-Butyl 5-(benzyloxy)-1H-indole-1-carboxylate,as a common compound, the synthetic route is as follows.

Example 93B; 5 -Hydroxy-indole- 1-carboxylic acid tert-butyl ester; [0464] A solution of the product of Example 93 A (680 mg, 2.103 mmol) in ethanol (20 mL) was treated with 10% palladium-on-carbon (68 mg) and ammonium formate (265 mg, 4.205 mmol), and stirred at room temperature under a nitrogen atmosphere for 1 hour. The reaction was filtered through a 0.45 mu PTFE membrane and the catalyst washed with methanol. The filtrate was concentrated by rotary evaporation under vacuum and the residue taken up in ethyl acetate (50 mL), washed with water (2 x 25 mL) and brine (25 mL), dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum to provide the title compound as a white solid (475 mg, 96%).

170147-29-2, The synthetic route of 170147-29-2 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; ABBOTT LABORATORIES; WO2007/76034; (2007); A2;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

170147-29-2, tert-Butyl 5-(benzyloxy)-1H-indole-1-carboxylate is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

ferf-Butyl 5-(benzyloxy)-1H-indole-1-carboxylate (5.75 g, 17.8 mmol), preparedaccording to the procedure described for Example 1, step 1, was added to a mixture of10% Pd/C in EtOH. Ammonium formate was added and the reaction stirred for 6 h. Themixture was filtered through Celite under a blanket of argon and the solvents were thenremoved. The residue was purified by flash chromatography to yield 3.5 g of ferf-butyl 5-hydroxy-1H-indole-1-carboxylate (74%). 1H-NMR (DMSO-d6) 5 9.19 (s, 1H), 7.84-7.78 (d,1H), 7.58-7.52 (d, 1H), 6.91 (s, 1H), 7.78-7.69 (m, 1H), 6.65-6.42 (m, 1H), 1.68-1.59 (s,9H).

170147-29-2, As the paragraph descriping shows that 170147-29-2 is playing an increasingly important role.

Reference：
Patent; BAYER PHARMACEUTICALS CORPORATION; WO2005/51957; (2005); A1;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1265231-91-1,3-(Dimethylamino)-2-(1-(phenylsulfonyl)-1H-indole-2-carbonyl)acrylonitrile,as a common compound, the synthetic route is as follows.

2-(1-Fluorocyclopropyl)-5-hydrazinyl-1H-benzo[d]imidazole dihydrochloride 10d (706mg, 2.5 3mmol) and (E)-3-(dimethylamino)-2-(1-(phenylsulfonyl)-1H-indole-2-carbonyl)acrylonitrile 1f (959mg, 2.53mmol, prepared according to the published patent application ) were suspended in 13mL of absolute ethanol, the reaction solution was refluxed for 4 hours. The reaction solution was cooled down to room temperature, solid precipitated. The solution was subjected to suction filtration, the filter cake was washed with ethanol (15mL*3) then was subjected to infrared drying to obtain (5-amino-1-(2-(1-fluoropropyl)-1H-benzo[d]imidazol-5-yl)-1H-pyrazol-4-yl)(1-(phenylsulfonyl)-1H-indol-2-yl)methanone 10e (493mg, black solid), yield: 36%. MS m / z (ESI): 540.8 [M + 1]

1265231-91-1, The synthetic route of 1265231-91-1 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Zhejiang Hisun Pharmaceutical Co., Ltd; CHEN, Lei; GUAN, Dongliang; BAI, Hua; YAN, Xing; MIAO, Shuai; ZHU, Songsong; (54 pag.)EP3339305; (2018); A1;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.192189-07-4,tert-Butyl 3-iodo-1H-indole-1-carboxylate,as a common compound, the synthetic route is as follows.

Triethyl borate (2.92 g, 20 mmol) was dissolved in tetrahydrofuran (20 mL) Cooled to -78 C, n-butyllithium (2.4 mol / L, 8.33 mL, 20 mmol) Stirred for half an hour, tert-butyl 3-iodo-lH-indole-1-carboxylate (3.43 g, LOmmol), slowly rose to room temperature, stirred for 2 hours, TLC detection of raw materials disappeared. Add water, ethyl acetate extraction, combined organic phase, Dried over anhydrous sodium sulfate, and the solvent was removed by rotary evaporation to give crude (2.61 g) Without purification directly for the next step, 192189-07-4

The synthetic route of 192189-07-4 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Shandong Xuanzhu Pharmaceutical Technology Co., Ltd.; Wu Yongqian; (29 pag.)CN104876914; (2017); B;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1059630-08-8,(4aS,9bR)-Ethyl 6-bromo-3,4,4a,5-tetrahydro-1H-pyrido[4,3-b]indole-2(9bH)-carboxylate,as a common compound, the synthetic route is as follows.

Example 5-A: Production of (6bR,10aS)-ethyI 2,3,6b,9,10,10a-hexahydro-2-oxo-lH- pyrido [3 ‘,4’ :4,5]-py rrolo [1 ,2,3-de] quinoxaline-8-carboxy late; Alternative to Example 5 above, (6bR, 1 OaS)-ethyl 3,6b,9, 10, 1 Oa- hexahydro-3 -methyl-2-oxo- 1 H-pyrido [3 ‘ ,4 ‘ :4,5]-pyrrolo [ 1 ,2,3 -de]quinoxaline-8- carboxylate may also be made in a one pot method starting from Compound of Formula ID. A 2 liter 4 neck round bottom flask is equipped with a mechanical stirrer, reflux condenser, N2 inlet, teflon covered K-type temperature probe with a controller, and a heating mantle. To the flask is charged (4aS,9bR)-ethyl 6-bromo-3,4,4a,5-tetrahydro- lH-pyrido[4,3-b]indole-2(9bH)-carboxylate (250 g, 769 mmol), chloroacetamide (124 g, 1153 mmol, 1.5 equiv), potassium iodide (191.5 g, 1160 mmol, 1.5 equiv), diisopropyl ethylamine (266 mL, 1531 mmol, 2.0 equiv), and dioxane (625 mL). The reaction is heated to reflux temperature of about 103 0C until less than 3% of the starting substrate is observed by HPLC (about 48 hours). Additional charge of N- methyl chloroacetamide and diisopropyl ethylamine maybe necessary. The reaction is then cooled to ca. 80 0C, and at this temperature copper iodide (29.2 g, 153.8 mmol, 0.2 equiv), potassium carbonate (232.5 g, 1682 mmol, 2.2 equiv), dimethylethylene diamine (49.6 mL, 461 mmol, 0.6 equiv), and additional dioxane (375 mL) is added. The reaction is then re-heated to reflux and is monitored by HPLC. Reflux occurs at ca. 103 0C. The reaction is monitored by HPLC.; Example 6-A: Production of (6bR,10aS)-ethyl 2,3,6b,9,10,10a-hexahydro-3-methyl- 2-oxo-lH-pyrido[3%4′:4,5]-pyrrolo[l,2,3-de]quinoxaline-8-carboxylate; Alternative to Example 6 above, (6bR, 1 OaS)-ethyl 3,6b,9, 10, 1 Oa- hexahydro-3-methyl-2-oxo-lH-pyrido[3′,4’:4,5]-pyrrolo[l,2,3-de]quinoxaline-8- carboxylate may also be made in a one pot method starting from Compound of Formula ID. A 2 liter 4 neck round bottom flask is equipped with a mechanical stirrer, reflux condenser, N2 inlet, teflon covered K-type temperature probe with a controller, and a heating mantle. To the flask is charged (4aS,9bR)-ethyl 6-bromo-3,4,4a,5-tetrahydro- lH-pyrido[4,3-b]indole-2(9bH)-carboxylate (250 g, 769 mmol), N-methyl chloroacetamide (124 g, 1153 mmol, 1.5 equiv), potassium iodide (191.5 g, 1160 mmol, 1.5 equiv), diisopropyl ethylamine (266 mL, 1531 mmol, 2.0 equiv), and dioxane (625 mL). The reaction is heated to reflux temperature of about 103 0C until less than 3% of the starting substrate is observed by HPLC (about 48 hours). Additional charge of N- methyl chloroacetamide and diisopropyl ethylamine maybe necessary. The reaction is then cooled to ca. 80 0C, and at this temperature copper iodide (29.2 g, 153.8 mmol, 0.2 equiv), potassium carbonate (232.5 g, 1682 mmol, 2.2 equiv), dimethylethylene diamine (49.6 mL, 461 mmol, 0.6 equiv), and additional dioxane (375 mL) is added. The reaction is then re-heated to reflux and is monitored by HPLC. Reflux occurs at ca. 103 0C. The reaction is monitored by HPLC.[0090] When complete, the reaction is cooled to ca. 40 0C and poured onto a plug of flash-grade silica gel (625 g, 2.5 g/g). It is eluted (under vacuum) with 6.25 L of ethyl acetate. The eluent is concentrated to a solid residue (320 gm), and then is dissolved in hot ethanol (800 ml). This mixture is allowed to cool to ambient temperature and stirred overnight. The next day it is cooled to 0-50C, aged for Ih and filtered. The cake is washed with cold ethanol (150 ml) and allowed to air dry to afford 170 grams (70%) of product as a white solid which is >99A% pure by HPLC. HPLC 10:90 to 90:10 CH3CN:H2O over 15 min. Hold at 90:10 for 2 min, 0.025% TFA Buffer, 1.5 mL/min, UV at 220 run, Phenomenex Jupiter Cl 8 column 4.6 mm x 250 mm. The product is 75A% pure by LC/MS in the total ion chromatogram. 1H-NMR (300MHz, CDCl3) 1.28(t, J= 6.9Hz, 3H), 1.86-1.96(m, 2H), 2.72(br, IH), 3.09-3.48(m, 7H), 3.86- 4.21(m, 5H), 6.75(dd, J= 1.2, 7.8Hz, IH), 6.82(t, J= 7.8Hz, IH), 6.90(dd, J= 1.2, 7.2Hz, IH).

1059630-08-8, The synthetic route of 1059630-08-8 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; INTRA-CELLULAR THERAPIES, INC.; WO2008/112280; (2008); A1;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

1265231-91-1, 3-(Dimethylamino)-2-(1-(phenylsulfonyl)-1H-indole-2-carbonyl)acrylonitrile is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,1265231-91-1

2-Cyclopropyl-5-hydrazinyl-1H-benzo[d]imidazole 1e (540mg, 2.06mmol) and 3-(dimethylamino)-2-(1-(phenylsulfonyl)-1H-indole-2-carbonyl)acrylonitrile 1f (581mg, 1.53mmol, prepared according to the published patent application ) were suspended in 30 mL of absolute ethanol, the reaction solution was refluxed for 6 hours. The reaction solution was cooled down to room temperature, solid precipitated. The solution was subjected to suction filtration, the filter cake was washed with 5mL of ethanol and then subjected to infrared drying to obtain (5-amino-1-(2-cyclopropyl-1H-benzo[d]imidazol-5-yl)-1H-pyrazol-4-yl)(1-(phenylsulfonyl)-1H-i ndol-2-yl)methanone 1g (675mg, tan solid), yield 67%. MS m / z (ESI): 522.8 [M + 1]

1265231-91-1 3-(Dimethylamino)-2-(1-(phenylsulfonyl)-1H-indole-2-carbonyl)acrylonitrile 68005411, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; Zhejiang Hisun Pharmaceutical Co., Ltd; CHEN, Lei; GUAN, Dongliang; BAI, Hua; YAN, Xing; MIAO, Shuai; ZHU, Songsong; (54 pag.)EP3339305; (2018); A1;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

1059630-08-8, (4aS,9bR)-Ethyl 6-bromo-3,4,4a,5-tetrahydro-1H-pyrido[4,3-b]indole-2(9bH)-carboxylate is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

1.000 equivalents of ethyl (4aS,9bR)-6-bromo-l,3,4,4a,5,9b-hexahydro-2H- pyrido[4,3-b]indole-2-carboxylate is charged into a reactor with 0.50 volumes of dimethylacetamide solvent at 20 C. A solution of 1.500 equivalents of N-methyl chloroacetamide in 0.30 volumes of dimethylacetamide is added, followed by 1.000 equivalents of potassium iodide, and 1.700 equivalents of diisopropylethylamine. The resulting suspension is heated at 102 C for 15 to 18 hours. After cooling to 45 C, 5.00 volumes of water are added. After further cooling and agitation, the product is isolated as a solid filter cake and is washed with additional water and dried under vacuum., 1059630-08-8

1059630-08-8 (4aS,9bR)-Ethyl 6-bromo-3,4,4a,5-tetrahydro-1H-pyrido[4,3-b]indole-2(9bH)-carboxylate 59317960, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; INTRA-CELLULAR THERAPIES, INC.; LI, Peng; ZHANG, Qiang; (113 pag.)WO2019/241278; (2019); A1;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles