Tag: M.W:200-300

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.923197-75-5,(6-Bromo-1H-indol-2-yl)methanol,as a common compound, the synthetic route is as follows.,923197-75-5

(6-Bromo-1H-indol-2-yl)methanol (80 mg, 0.35 mmol) and dess-martin periodinane (178 mg, 0.42 mmol) were dissolved in dichloromethane (10 mL), and it was stirred for 30 minutes at room temperature. The reaction mixture was diluted with ethyl acetate, and it was washed with 10% sodium thiosulfate, saturated NaHC03and brine. The organic layer was dried over Na2S04, and it was concentrated under reduced pressure. The residue was purified on an ISCO chromatograph (0-10% ethyl acetate/hexane) to give product as a white solid (78 mg, 100%);1H NMR (300 MHz) (CDCb) d 9.86 (s, 1H), 9.23 (bs, 1H), 7.65 (s, 1H), 7.61 (d, J= 9 Hz, 1H), 7.29 (d, j= 9 Hz, 1H), 7.26-7.25 (m, 1H).

923197-75-5 (6-Bromo-1H-indol-2-yl)methanol 13567957, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; RUTGERS, THE STATE UNIVERSITY OF NEW JERSEY; TAXIS PHARMACEUTICALS, INC.; LAVOIE, Edmond, J.; SAGONG, Hye Yeon; PARHI, Ajit, K.; (144 pag.)WO2019/99402; (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.1065181-58-9,Ethyl 5-bromo-1H-indole-7-carboxylate,as a common compound, the synthetic route is as follows.

Intermediate 104:Ethyl 5-bromo-3-(tetrahydro-3-thienylmethyl)-1 H-indole-7-carboxylate.To a solution of tetrahydro-3-thiophenecarbaldehyde (5.0 g, 43.10 mmol) in dichloromethane (200 mL) was added TMS-OTf (15.4 mL, 86.26 mmol) and ethyl 5- bromo-1 H-indole-7-carboxylate (11.5 g, 43.10 mmol) dropwise at 0 0C. The mixture was stirred at 0 0C for 2h, and then triethylsilane was added at the same temperature, which was maintained for 2h. The reaction was warmed to 20 0C and stirred for 16h. Water was added, the layers were separated, and the organic layer was (Na2SO4),concentrated, and purified on silica gel (PE:EA = 50:1 ), giving 9g (56.4) of the title compound. 1H NMR (CDCI3): delta 1.43 (t, 3H), 2.08 (m, 1 H), 2.58 (m, 2H), 2.88 (m, 6H), 4.44 (q, 2H), 7.09 (s, 1 H), 7.89 (s, 1 H), 7.95 (s, 1 H), 9.65 (s, 1 H).

1065181-58-9, As the paragraph descriping shows that 1065181-58-9 is playing an increasingly important role.

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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.289483-82-5,4-Methyl-7-nitro-1H-indole-3-carbonitrile,as a common compound, the synthetic route is as follows.

Reference Example 3A; Synthesis of 7-amino-3-cyano-4-methyl-1H-indole; After suspending 12.6 g (62.6 mmol) of the 3-cyano-4-methyl-7-nitro-1H-indole obtained in Reference Example 2A in a mixture of 100 mL of tetrahydrofuran and 100 mL of methanol, the suspension was subjected to hydrogenation in the presence of 430 mg (1.87 mmol) of platinum oxide at ordinary temperature, 3 atmospheres. The catalyst was removed by filtration, the filtrate was concentrated to dryness, and then a mixture of tert-butyl methyl ether and hexane was added to the residue and the crystals were collected by filtration to give 10.7 g of the title compound (yield: 99.8%). 1H-NMR (DMSO-d6) delta (ppm): 2.47 (3H, s), 5.07 (2H, s), 6.34 (1H, d, J=7.6Hz), 6.64 (1H, d, J=7.6Hz), 8.10 (1H, s), 11.70 (1H, br s).

289483-82-5, 289483-82-5 4-Methyl-7-nitro-1H-indole-3-carbonitrile 11622527, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; Hayashi, Kenji; Abe, Taichi; Ozeki, Naoki; Akamatsu, Hiroshi; US2007/37854; (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

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 Intermediate 1(500 mg, 2.04 mmol) in CH3COOH (20 mL) was added NBS (381 mg, 2.14 mmol) and then stirring at rt overnight. The mixture was poured intoH20 (100 mL), filtered to afford 8-bromo-1-chloro-5H-pyrido[4,3-bjindole-4- carboxamide.1HNMR (300MHz, DMSO-d6) oe12.30 (s, 1H), 8.80 (s,1 H),8.46 (s, 1 H), 8.35- 8.38 (m, 1 H), 7.69-7.82 (m, 3 H) ppm.

As the paragraph descriping shows that 938465-52-2 is playing an increasingly important role.

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

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

Example 558 52 mg of tert-butyl 5-hydroxy-1H-indole-1-carboxylate, 79 mg of tripotassium phosphate, 4.7 mg of 2-(di-tert-butylphosphino)-2′,4′,6′-triisopropylbiphenyl and 6.8 mg of tris(dibenzylideneacetone)dipalladium(0) were added to 1.4 mL of toluene solution containing 70 mg of tert-butyl 2-(benzamido)-4-bromobenzoate at room temperature, and the resulting mixture was heated to reflux under nitrogen atmosphere for 2 hours and 30 minutes. After the reaction mixture was cooled to room temperature, ethyl acetate and 10% citric acid aqueous solution were added and insoluble were removed by filtration. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with a saturated sodium chloride aqueous solution, and the solvent was evaporated under reduced pressure. The obtained residue was purified with silica gel column chromatography [PSQ100B (spherical) manufactured by Fuji Silysia Chemical Ltd., eluent; hexane: ethyl acetate = 10:1] to obtain tert-butyl 5-(3-(benzamido)-4-(tert-butoxycarbonyl)phenoxy)-1H-indole-1-carboxylate., 434958-85-7

The synthetic route of 434958-85-7 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; TOYAMA CHEMICAL CO., LTD.; EP1820795; (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

16732-69-7, Ethyl 7-bromo-1H-indole-2-carboxylate is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

c (R)-7-Bromo-1-(2-tert-butoxycarbonylamino-1-methyl-ethyl)-1H-indole-2-carboxylic acid ethyl ester A solution of 8.1 g (30.1 mmol) 7-bromo-1H-indole-2-carboxylic acid ethyl ester in 120 ml N,N-dimethylformamide was cooled to 0 C. and 3.55 g (31.6 mmol) potassium tert-butoxide was added. After 30 min., 7.86 g (33.1 mmol) (S)-5-methyl-2,2-dioxo-[1,2,3]oxathiazolidine-3-carboxylic acid tert-butyl ester were added and the cooling bath was removed. After 20 h the reaction mixture was poured on 10% aqueous citric acid solution and ethyl acetate. The organic layer was dried over magnesium sulfate, filtered and evaporated. The resulting yellow oil was chromatographed on silica gel (0.032-0.063 mm) with tert-butyl methyl ether: n-hexane (1:8) as eluant to give the desired compound as a yellow oil. ISP-MS: m/e=427.3 ([M+H+])., 16732-69-7

The synthetic route of 16732-69-7 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Hebeisen, Paul; Mattei, Patrizio; Muller, Marc; Richter, Hans; Roever, Stephan; Taylor, Sven; US2002/169163; (2002); 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.,1065181-58-9

Intermediate 98:Ethyl 5-bromo-3-(tetrahydro-2H-thiopyran-3-ylmethyl)-1H-indole-7-carboxylate.To a 100 ml. three-necked flask equipped with an addition funnel was added tetrahydro- 2H-thiopyran-3-carbaldehyde (2.50 g, 0.019 mol) and dry DCM (30 ml_). Trimethylsilyl trifluoromethanesulfonate was put in the addition funnel. The mixture was cooled down to0 0C with an ice bath and put under nitrogen atmosphere. Trimethylsilyl trifluoromethanesulfonate was added over 15 min, and 10 ml. of dry DCM were used to wash the addition funnel walls. A solution of ethyl 5-bromo-1 H-indole-7-carboxylate in 30 ml. dry DCM was added to the mixture for 2 h at 0 0C, and the mixture was then stirred at room tmperature overnight. An aqueous solution of sodium bicarbonate was added, the layers were separated, and the mixture was extracted with DCM (3 x 100 ml_). The combined organic layers were dried (Na2SO4), filtered, and purified by chromatography, eluting with a mixture of PE:EA (50:1-30:1 ) to afford 4.82 g (66.0%) of the title compound. 1H NMR NMR (CDCI3) delta 1.1 1-1.15 (m,1 H),1.43 (t,3H),1.65-1.71 (m,2H),1.83-1.87 (m,1 H),1.96-2.03 (m,2H), 2.32-2.38 (m,1 H), 2.51-2.59 (m, 2H),2.66-2.68 (m, 2H), 4.40-4.45 (q,2H), 7.07 (d, 1 H),7.77 (d, 1 H), 7.95 (d, 1 H), 9.64 (s, 1 H).

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

1065181-58-9, Ethyl 5-bromo-1H-indole-7-carboxylate is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Intermediate 72:(racem/cJ-Ethyl 5-bromo-3-(2,2-dimethyltetrahydro-2H-thiopyran-4-yl)-1H-indole-7- carboxylate.2,2-Dimethyltetrahydro-4H-thiopyran-4-one (0.675 g, 4.68 mmol) was placed in a dried flask fitted up with an addition funnel, a septum and an argon inlet, and dissolved in dry DCM (15 mL), cooled to 0 0C, stirred, and then trimethylsilyl trifluoromethanesulfonate (1.692 mL, 9.36 mmol) was added dropwise through the addition funnel over 10 minutes. DCM (5 mL) was used to wash the addition funnel walls. To this mixture was added dropwise ethyl 5-bromo-1 H-indole-7- carboxylate (1.341 g, 5 mmol) in DCM (15 mL) over 2 hours. Then triethylsilane (2.98 mL, 18.73 mmol) was added in one portion. The mixture was stirred 2 h at 0 0C, and left stirring at 23 0C overnight. The reaction was quenched with a saturated aqueous solution of sodium bicarbonate, and the resulting biphasic mixture extracted with DCM to give 2.1 15 g of the title compound. LC/MS: m/z 398.0 (M+H), Rt 1.49 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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.14618-45-2,3-(Trifluoroacetyl)indole,as a common compound, the synthetic route is as follows.

14618-45-2, General procedure: One of compounds 3a-3f (20 mmol) was dissolved in DMF (10 mL). Trifluoroacetic anhydride (4.2 mL, 30 mmol) was added dropwise at 0C. After stirring for 3.5 h, water was added, the solid filtered off and treated with 20% NaOH (40 mL, 0.2 mol) at 55C overnight. Upon cooling down, the solution was extracted with Et2O. The aqueous phase was acidified with concentrated HCl and the residue was filtered off to give one of compounds 4a-4f. 1H-Indole-3-carboxylic acid (4a). White solid, yield 81%, mp 216-218C (214C [20]). 1H NMR spectrum, delta, ppm: 7.15 t (J = 8.0 Hz, 2H, ArH), 7.45 d (J = 8.0 Hz, 2H, ArH), 8.00 s (1H, CH-N), 11.81 s (1H, COOH), 11.93 s (1H, NH).

14618-45-2 3-(Trifluoroacetyl)indole 589126, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Letter; Zhang; Xu; Wang; Kang; Russian Journal of General Chemistry; vol. 87; 12; (2017); p. 3006 – 3016;,
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.380448-07-7,5-Chloro-3-formyl-1H-indole-2-carboxylic acid,as a common compound, the synthetic route is as follows.,380448-07-7

REFERENTIAL EXAMPLE 287 5-Chloro-2-ethoxycarbonylindole-3-carboxylic acid: The compound (1.5 g) obtained in Referential Example 286 and sulfamic acid (1.7 g) were dissolved in tert-butanol (30 ml)-water (30 ml), and sodium chlorite (1.6 g) was added to stir the mixture for 8 hours. The reaction mixture was diluted with water and extracted with ethyl acetate, and the extract was successively washed with 1N hydrochloric acid and saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was recrystallized from a mixed solvent of isopropyl ether and hexane to obtain the title compound (0.7 g). 1H-NMR (DMSO-d6) delta: 1.34(3H,t,J=7.1 Hz), 4.38(2H,q,J=7.1 Hz), 7.33(1H,dd,J=8.0, 1.4 Hz), 7.52(1H,d,J=8.0 Hz), 7.97(1H,d,J=1.4 Hz), 12.75(1H,br).

As the paragraph descriping shows that 380448-07-7 is playing an increasingly important role.

Reference：
Patent; DAIICHI PHARMACEUTICAL CO., LTD.; US2005/20645; (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