Tag: M.W:200-300

434958-85-7, N-Boc-5-Hydroxyindole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,434958-85-7

To a mixture of N-Boc-5-hydroxyindole (5.0 g), 1-piperidinepropanol (4.95 mL), Toluene (100 mL) and THF (25 mL), cyanomethylenetributylphosphorane (7.3 mL) was added and the mixture was stirred first at 85 C. for 3 hours, then at 100 C. for 3 hours, and finally at room temperature overnight. The reaction mixture was concentrated under reduced pressure and the resulting residue was purified by silica gel column chromatography (SNAP Cartridge KP-Sil, 100 g) to give the titled compound (3.97 g). MS (ESI pos.) m/z: 359([M+H]+)

As the paragraph descriping shows that 434958-85-7 is playing an increasingly important role.

Reference：
Patent; TAISHO PHARMACEUTICAL CO., LTD; Yoshinaga, Mitsukane; Ishizaka, Tomoko; Wakasugi, Daisuke; Shirokawa, Shin-ichi; Hattori, Nobutaka; Kashiwa, Shuhei; Kuwada, Takeshi; Shimazaki, Youichi; US2015/45551; (2015); 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.10075-48-6,5-Bromo-3-methyl-1H-indole,as a common compound, the synthetic route is as follows.

Step B: 5-Bromo-1,3-dimethylindole To a stirred solution of 5-bromo-3-methylindole (2.85 g., 13.6 mmol., 1eq.) in DMF (35 mL.) was added NaH (651 mg. of a 60% dispersion in oil, 16.28 mmol., 1.2 eq.). The mixture was stirred 15 minutes. To this mixture was added iodomethane (0.930 mL., 14.93 mmol., 1.1 eq.). The mixture was stirred for 2 hours. The DMF was removed in vacuo. The residue was diluted with water and extracted 4* with Et2 O. The organic extracts were combined, dried over anhydrous MgSO4, filtered and concentrated in vacuo giving 3.04 g. 5-bromo-1,3-dimethylindole as a reddish liquid.

10075-48-6, As the paragraph descriping shows that 10075-48-6 is playing an increasingly important role.

Reference：
Patent; Merck & Co., Inc.; US5349061; (1994); A;,
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

393553-57-6, 6-Bromo-4-methoxy-1H-indole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,393553-57-6

A solution of 6-bromo-4-methoxyindole (1, 100mg, 0.44mmol) and N-(2,2-dimethoxyethyl)-trifluoroacetamide16 (178mg, 0.88mmol, 2.0 equiv) in dichloromethane (3.0mL) was added to a solution of triethylsilane (0.43mL, 2.64mmol, 6 equiv) and TFA (0.17mL, 2.21mmol, 5 equiv) in dichloromethane (2.0mL). The reaction mixture was stirred at room temperature for 3h, cooled down to 0C and then neutralized with a saturated solution of sodium bicarbonate (?75mL). The aqueous phase was extracted with dichloromethane (3×50mL) and the combined organic phases washed with brine, dried (Na2SO4), filtered and concentrated in vacuo. Purification by column chromatography on silica gel eluting with ethyl acetate-petroleum ether (1:3) gave the title compound (83mg, 0.23mmol, 51%) as light yellow solid, M.p. 111.3-113.1C; HRMS [ESI, (M+Na)+] found 386.9925; [C13H1279BrF3N2O2+Na]+ requires 386.9926; numax (neat)/cm-1 3434, 3343, 2938, 2885, 1690, 1615, 1175, 978, 795; deltaH (500MHz, CDCl3) 8.07 (1H, br s, NH), 7.17 (1H, d, J 1.4, CH), 6.96 (1H, br s, NH), 6.89 (1H, d, J 2.3, CH), 6.65 (1H, d, J 1.4, CH), 3.94 (3H, s, Me), 3.62 (2H, dd, J 12.0, 5.7, CH2), 3.12 (2H, dd, J 9.3, 3.4, CH2); deltaC (100MHz, CDCl3) 154.2 (C=O), 138.5 (C), 122.0 (CH), 116.12 (C), 116.10 (C), 113.1 (C), 108.3 (CH), 104.3 (CH), 55.7 (Me), 42.2 (CH2), 25.4 (CH2), 2 x C not observed

The synthetic route of 393553-57-6 has been constantly updated, and we look forward to future research findings.

Reference：
Article; Nabi, Ardalan A.; Liyu, Jessica; Lindsay, Ashley C.; Sperry, Jonathan; Tetrahedron; vol. 74; 12; (2018); p. 1199 – 1202;,
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

101861-63-6, 4,6-Dichloroindole-2-carboxylic acid is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example IPreparation of 4, 6-dichloro-N-(4, 4-dimeth ylcyclohexyl)- IH-indole-2-carboxamide (IA): (1A)A mixture of 4,6-dichloro-1 H-indole-2-carboxylic acid -1d: 205 g, 891 .1 mmol in 9 batches) and 4,4-dimethylcyclohexylamine.HCI -6b: 160.4 g, 980.2 mmol) in dry DMF (2290 mL) was cooled to 000 and added HATU (406.3 g, 1070 mmol) followed by5 DIPEA (775.5 mL, 4450 mmol) drop-wise and the mixture was stirred under inert atmosphere at room temperature for 17 h. Ice-cold water (7000 mL) was added to the reaction mixture and stirred vigorously and the precipitated solid was collected by filtration and dried thoroughly. The combined crude solids from all batches were purified by column chromatography over silica gel (100-200 mesh) using a solvent gradient of10 30%-40% ethyl acetate in hexanes as eluentto afford 213 g of light brown solid. It was triturated with ether/hexanes (3:7) in five cycles to give off-white solid. The solid was treated with charcoal in ethyl acetate/methanol (4:1) at 70C for 3h and filtered to afford 207 g (68.5%) of 4,6-dichloro-N-(4,4-dimethylcyclohexyl)-1 H-indole-2-carboxamide (IA) as a white solid.15 NMR (400 MHz, DMSO-d6): 6 12.06 (5, 1 H), 8.44 (d, J = 8.0 Hz, 1 H), 7.41 (5,1 H), 7.30 (5, 1 H), 7.22 (5, 1 H), 3.80-3.65 (m, 1 H), 1 .70-1 .60 (m, 2H), 1.60-1 .45 (m, 2H),1.45-1.35 (m, 2H), 1.35-1.20 (m, 2H), 0.95 (5, 3H), 0.93 (5, 3H). 130 NMR (100 MHz,DMSO-d6): 6159.3, 136.7, 133.7, 127.5, 126.2, 124.8, 119.3, 111.1, 100.6, 48.1, 37.6(20), 32.1, 29.3 (20), 28.1 (20). ESI MS: m/z 339.01 [(Mi-H] & 341 .03 [(M+2)+H]. HPLC 20 purity: 99.7%.

101861-63-6, The synthetic route of 101861-63-6 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; NOVARTIS AG; JIRICEK, Jan; KONDREDDI, Ravinder Reddy; SMITH, Paul William; WO2014/37900; (2014); 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

938465-52-2, 1-Chloro-5H-pyrido[4,3-b]indole-4-carboxamide is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

938465-52-2, To a solution of (S)-2-(4-fluorophenyl)-2,8-diazaspiro[5.Sjundecan-1-one (120 mg, 0.45 mmol) in NMP (3 mL) was added 1-chloro-5H-pyrido[4,3-bjindole-4-carboxamide(Intermediate 1, 123 mg, 0.Smmol) and DIPEA (174 mg, 1.35 mmol), and the mixture was heated under microwave irradiation for 1.5 h at 150 C.The mixture was purified with prepHPLC to give (R)- 1 -(8-(4-fluorophenyl)-7-oxo-2, 8-diazaspiro[5 .51 undecan-2-yl)-5H-pyrido [4,3- bjindole-4-carboxamide. MS: 472.3 [M+Hjt 1H NMR (400 MHz, CD3OD) 3 8.45 (s, 1H), 8.03 (d, fr8.0 Hz, 1H), 7.81 (d, fr8.0 Hz, 1H), 7.62 (t, J=7.3 Hz, 1H), 7.55 – 7.49 (m, 1H), 7.11 – 7.06(m, 4H), 4.28 (d, J=12.5 Hz, 1H), 4.03 – 3.93 (m, 1H), 3.87 (d, fr12.5 Hz, 1H), 3.80 (d, fr4.8Hz, 1H), 3.63 – 3.53 (m, 2H), 2.43 (ddd, fr4.8, 7.7, 12.9 Hz, 1H), 2.25 – 2.07 (m, 3H), 2.07 -1.98 (m, 3H), 1.94 – 1.84 (m, 1H) ppm.

938465-52-2 1-Chloro-5H-pyrido[4,3-b]indole-4-carboxamide 59198457, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; MERCK SHARP & DOHME CORP.; LIU, Jian; KOZLOWSKI, Joseph; KIM, Ronald; GAO, Xiaolei; BOGA, Sobhana Babu; YU, Younong; WU, Hao; LIU, Shilan; YANG, Chundao; (102 pag.)WO2016/164284; (2016); 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.1065181-58-9,Ethyl 5-bromo-1H-indole-7-carboxylate,as a common compound, the synthetic route is as follows.

Intermediate 87:Ethyl 5-bromo-3-(2-phenyltetrahydro-2H-thiopyran-4-yl)-1H-indole-7-carboxylate.To a solution of 2-phenylthian-4-one (SJTU) (0.900 g, 4.68 mmol) in dichloromethane (DCM) (15 ml_), cooled on an ice bath to 0 0C, under argon, was added dropwise trimethylsilyl trifluoromethanesulfonate (1.807 ml_, 10 mmol) over 10 minutes, an additional portion of dry DCM (5 ml.) was used to wash the addition funnel walls. To this mixture ethyl 5-bromo-1 H-indole-7- carboxylate (1.340 g, 5.00 mmol) was added dropwise, in solution with of dry DCM, over 2 hours. Finally, triethylsilane (3.19 ml_, 20 mmol) was added in one portion and the mixture was stirred 2 h at ca 0 0C, and left stirring at 23 0C 16 h. The reaction was quenched with a saturated aqueous solution of sodium bicarbonate, and the resulting biphasic mixture partitioned with DCM to afford 2.21 g of brow gummy oil. LCMS of product may indicate an overlapping mixture of ca 5:2 major to minor isomers (cis/trans). LC/MS: m/z 448.1 (M+H), Rt 3.23 min., 1065181-58-9

1065181-58-9 Ethyl 5-bromo-1H-indole-7-carboxylate 59332585, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; SMITHKLINE BEECHAM CORPORATION; WO2008/118724; (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

6127-19-1,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.6127-19-1,6-Bromo-2-methyl-1H-indole,as a common compound, the synthetic route is as follows.

COMPARATIVE EXAMPLE 4 Synthesis of 6-bromo-2-methylindole In a reaction flask the atmosphere inside of which was substituted by nitrogen, 1.31 g (5.1 mmol) of 4-bromo-2-nitrophenylacetone, 10 g of 1-butanol and 0.065 g of 5% palladium supported on active carbon [manufactured by N.E. CHEMCAT CORPORATION (50% water-containing product)] were placed, hydrogen gas was supplied therein at ordinary pressure and 90 C., and the resulting mixture was reacted for 5 hours. After confirming the disappearance of 4-bromo-2-nitrophenylacetone with liquid chromatography, the atmosphere was substituted by nitrogen, and the catalyst was filtered off through celite. The reaction solution was subjected to quantitative analysis with liquid chromatography, and as a result of it, 6-bromo-2-methylindole was not obtained at all, and a mixture composed of many products including 2-methylindole that bromine atom was eliminated, and the like was obtained.

The synthetic route of 6127-19-1 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Nissan Chemical Industries, LTD.; US2007/83053; (2007); 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

1000340-33-9, 3,4-Dibromo-7-azaindole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Method B:A mixture of 3,4-dibromo-lH-pyrrolo[2,3-b]pyridine (D2) (1.014 g, 3.67 mmol), SEMC1 (0.650 mL, 3.67 mmol) and DIPEA (1.280 mL, 7.35 mmol) in DCM (12.54 mL) was stirred at RT under nitrogen for overnight (17 hours). TLC showed presence of starting material. Stirring continued for 3 hours. TLC showed that the reaction has completed. The reaction mixture was taken up in DCM and purified using silica gel, eluting with ethyl acetate in cyclohexane (0 to 20%). Fractions with desired product were collected and solvent reduced in vacuo to afford the title compound (0.527 g). LCMS (A): m/z (M+H)+ 407, C13H18Br2N20Si requires 406 (basic)., 1000340-33-9

1000340-33-9 3,4-Dibromo-7-azaindole 24729560, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; GLAXO WELLCOME MANUFACTURING PTE LTD; CHEN, Deborah, W.; DUNCAN, Sarah; KING, Nigel, Paul; LEE, Kiew, Ching; MAK, Sing, Yeung; RIVERS, Dean, Andrews; WO2012/170752; (2012); 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

4792-71-6, 5,7-Dichloro-1H-indole-2-carboxylic acid is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 102 R-Methyl 2-[(5-7-dichloro-1H-indole-2-carbonyl)-amino]-3-phenyl-propionate From 5,7-dichloro-1H-indole-2-carboxylic acid and D-phenylalanine methyl ester. 1H NMR (300 MHz, CDCl3) delta 3.25 (m, 2H), 3.80/3.95 (s, 3H), 5.10 (m, 1H), 6.62 (d, 6 Hz, 1H), 6.69 (d, 2 Hz, 1H), 7.10 – 7.15 (m, 2H), 7.25 – 7.35 (m, 3H), 7.50 – 7.56 (s, 1H), 9.35 (br, 1H)., 4792-71-6

The synthetic route of 4792-71-6 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; PFIZER INC.; EP1134213; (2001); 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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1065181-58-9,Ethyl 5-bromo-1H-indole-7-carboxylate,as a common compound, the synthetic route is as follows.

Intermediate 25:Ethyl 5-bromo-3-(tetrahydro-3-thienyl)-1H-indole-7-carboxylate.Dihydro-3(2H)-thiophenone (0.381 g, 3.73mmol) was dissolved in dichloromethane (50ml) in an oven dried flask containing 3A molecular sieves and stirred under Argon at O0C. TMS-OTf (0.826g, 3.73mmol, 0.67 ml.) was added slowly to the mixture over 10 min. Ethyl 5-bromo-1 /-/-indole-7-carboxylate (1 g, 3.73mmol) was dissolved in DCM (6 ml.) and added to the reaction via syringe pump over 2 hours, after which it was stirred for 30 min at 0 0C. Triethylsilane (0.651 g, 0.89ml, 5.59mmol) was then added all at once and the reaction was stirred at room temperature for 18 hours. The reaction was then quenched with a saturated sodium bicarbonate solution (35 ml.) and extracted with DCM (2 x 50 ml_). The combined organics were washed with water (2 x 100 ml_), brine, dried with MgSO4, and concentrated. The crude compound was purified on Combiflash silica column with 10% EA/Hexane to give 0.62Og (47%) of the title compound. LCMS m/z =355 (M+H), RT = 1.34 min., 1065181-58-9

The synthetic route of 1065181-58-9 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; SMITHKLINE BEECHAM CORPORATION; WO2008/118724; (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