Month: March 2022

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.2795-41-7,6-Fluoroindole-3-carboxaldehyde,as a common compound, the synthetic route is as follows.

To a stirring solution of 6-fluoro- ?H-indole-3 -carbaldehyde SM 1 (1 .0 g, 6 mmol) in 50% EtOH/H20 (20 mL) was added (NH4)2C03 (3.0 g, 30 mmol) followed by potassium cyanide (0.6 g, 9 mmol) at room temperature. The reaction mixture was heated to 75 C for 18 h. After consumption of the starting material (by TLC), the reactionmixture was diluted with water and extracted with EtOAc. Combined organic extracts weredried over anhydrous Na2504 and concentrated under reduced pressure to obtain crudeproduct, which was purified by silica gel column chromatography eluting with 10%MeOH/DCM to afford compound 1(0.67 g, 47 %) as a white solid. LC-MS: m/z = 234.1[(M+1)].

2795-41-7, As the paragraph descriping shows that 2795-41-7 is playing an increasingly important role.

Reference：
Patent; ABBVIE INC.; KESICKI, Edward A.; WANG, Ce; PATANE, Michael A.; KLUGE, Arthur F.; VAN DRIE, JR., John H.; (121 pag.)WO2016/44777; (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

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

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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.399-51-9,6-Fluoro-1H-indole,as a common compound, the synthetic route is as follows.

To reactor A were charged diethoxymethane (DEM)(65 mE, 0.52 mol), water (50 mE) and formic acid (39 mE, 1.02 mol)). The mixture was heated at approx. 80 C. (reflux) for approx. 2 h and then cooled to approx. 20 C. To reactor B were charged 6-fluoroindole (50 g, 0.37 mol) and 80% acetic acid (66 mE, 1.17 mol). The suspension was cooled to 2-5 C. 40% Aq. dimethylamine (103 mE, 2.04 mol) was added drop- wise to reactor B keeping the temperature below approx. 15 C. The reaction mixture was stirred for approx. 20 mm and at the same time the temperature was adjusted to 2-4 C. The mixture from reactor A (DEM, water, formic acid, formaldehyde and ethanol at about 20 C.) was added drop-wise to reactor B while keeping the temperature at 2-8 C. The reaction mixture was stirred for additional 10 mm at 2-8 C. The reaction mixture was slowly warmed to approx.40 C. over a 1 h period. The reaction mixture was stirred at approx. 40C. for an additional 1 h. The reaction mixture was cooled to about 20 C. To reactor C was charged aq. NaOH (800 mE, 2.40 mol, 3 M) and the solution was cooled to about 10 C. The reaction mixture from reactor B was added dropwise to the NaOH solution in reactor C while keeping the temperature at 10-15C. (pH>14). The suspension was stirred for 40 mm at 5-20C. (pH>1 4). The product was collected by filtration and the filter-cake was washed twice with water (2×250 mE). The product was dried at approx. 60 C. under vacuum for 16 h to yield Compound (II) (67.6 g, 95%) with 98% UV purity in HPLC analysis., 399-51-9

As the paragraph descriping shows that 399-51-9 is playing an increasingly important role.

Reference：
Patent; H. Lundbeck A/S; JACOBSEN, Mikkel Fog; NIELSEN, Ole; (16 pag.)US2016/168089; (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

162100-95-0, 6-Fluoro-5-methyl-1H-indole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Diethylaluminium chloride 1M in hexane (15 mL, 15.1 mmol) was added dropwise at 000 to a solution of 6-fluoro-5-methyl-1 H-indole [CAS 162100-95-0] (1 .5 g, 10.6mmol) in CH2CI2 (30 mL). After 30 mm at 0C, 2-(4-fluoro-2-methoxyphenyl)acetyl chloride Ia? (3.05 g, 15.1 mmol, synthesis: see Example 1) in CH2CI2 (20 mL) was added slowly at 0C. The reaction was stirred at 0C for 3 h and then at room temperature for 1 h. Ice-water was added. The precipitate was filtered off, washed with water and dried under vacuum to afford 2-(4-fluoro-2-methoxyphenyl)-1 -(6-fluoro-5-methyl-1 H-indol-3-yl)ethanone 3a (2.27 g).

162100-95-0, 162100-95-0 6-Fluoro-5-methyl-1H-indole 2774611, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; JANSSEN PHARMACEUTICALS, INC.; KATHOLIEKE UNIVERSITEIT LEUVEN; BARDIOT, Dorothee Alice Marie-Eve; BONFANTI, Jean-Francois; COESEMANS, Erwin; KESTELEYN, Bart Rudolf Romanie; MARCHAND, Arnaud Didier M; RABOISSON, Pierre Jean-Marie Bernard; (96 pag.)WO2017/167952; (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.39689-58-2,2-(1H-Indol-6-yl)acetic acid,as a common compound, the synthetic route is as follows.

39689-58-2, General procedure: to a solution of the substituted acid in DMF (0.25 mmol/mL) were added DMAP (2 to 4 equiv), EDCI.HCI (1 to 1.5 equiv) and the substituted amine (1 equiv). The reaction mixture was stirred at rt. After completion of the reaction (monitored by TLC), sat. NH4CI or HCI 0.5N was added and the solution was extracted with EtOAc. The organic layer was washed with sat. NH4CI, dried over Mg504, filtered and evaporated to dryness underreduced pressure (Figure 3AA).

As the paragraph descriping shows that 39689-58-2 is playing an increasingly important role.

Reference：
Patent; GENFIT; DELHOMEL, Jean-Francois; PERSPICACE, Enrico; MAJD, Zouher; PARROCHE, Peggy; WALCZAK, Robert; (284 pag.)WO2018/138362; (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

31241-19-7, 5-Methoxy-2,3,3-trimethyl-3H-indole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,31241-19-7

5-methoxy-2,3,3-trimethyl-3H-indole (2g, 10.6mmol) with1,4-butyl sultone (4.3 g, 31.7 mmol) was dissolved in 40 mL of toluene.The temperature was raised to 120 C and refluxed for 50 h.After the reaction, the mixture was filtered to give an off-white solid.Purified by column chromatography to give a pale yellow solid2-1 1.9g.

The synthetic route of 31241-19-7 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Shenyang Pharmaceutical University; Wang Dun; Wang Yongjun; Yang Xiaoguang; Lv Qingzhi; (25 pag.)CN108752319; (2018); 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

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.1008-07-7,7-Chloro-1H-indole-3-carbaldehyde,as a common compound, the synthetic route is as follows.

We heated a mixture of (1-6) (1 mmol) and l-methylimidazol-255(l,3H)- dione (which we synthesized according to the method used by Janin et al., Eur. J. Org. Chem. 2002:1763-1769, 2002) (250mg, 2.5 mmol) in piperidine (2 mL) at 1100C for four hours under an argon atmosphere. Then, we allowed the reaction mixture to cool in a refrigerator (~ 5C) with the addition of ether (2 mL). We filtered the precipitate and washed it with ether to give (1-7). 1H NMR (500 MHz, DMSO-d6): delta 12.15 (IH, br s), 10.26 (IH, br s), 8.23 (IH, s), 7.79 (IH, d, J = 8.0 Hz), 7.27 (IH, d, J = 8.0 Hz,), 7.13 (IH, t, J = 7.8 Hz), 6.82 (IH, s), 2.97 (3H, s).

1008-07-7, The synthetic route of 1008-07-7 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; PRESIDENT AND FELLOWS OF HARVARD COLLEGE; THE BRIGHAM AND WOMEN’S HOSPITAL, INC.; WO2007/75772; (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

900514-08-1, 5-Chloro-3-iodo-7-azaindole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

900514-08-1, To a solution of 5-chloro-3-iodo-1H-pyrrolo[2,3-b]pyridine (2, 5.00 g, 18.0 mmol) in 80.0 mL of N,N-dimethylformamide, sodium hydride (1.1 g, 60% in mineral oil, 27.0 mmol) was added slowly. A solution of benzenesulfonyl chloride (11, 2.40 mL, 18.8 mmol) in 10.0 mL of N,N-dimethylformamide was added dropwise at 0 C. The reaction mixture was stirred at room temperature for 15 hours, then poured into ice water and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, filtered and the filtrate concentrated under vacuum. The resulting solid was washed with 5% ethyl acetate in hexane, isolated by filtration, and dried to provide the desired compound (12, 5.9 g). 1H NMR was consistent with the compound structure. 1-Benzenesulfonyl-3-iodo-5-methyl-1H-pyrrolo[2,3-b]pyridine 13

900514-08-1 5-Chloro-3-iodo-7-azaindole 24229220, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; Plexxikon Inc.; Zhang, Jiazhong; Ibrahim, Prabha N.; Bremer, Ryan; Spevak, Wayne; Cho, Hanna; US9096593; (2015); B2;,
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