1H-Pyrrolo[2,3-b]pyridine-3-carboxylic acid, 5-broMo-2-Methyl-1-(phenylsulfonyl)-, Methyl ester synthesis

8synthesis methods

Product Name:1H-Pyrrolo[2,3-b]pyridine-3-carboxylic acid, 5-broMo-2-Methyl-1-(phenylsulfonyl)-, Methyl ester
CAS Number:1200130-72-8
Molecular formula:C16H13BrN2O4S
Molecular Weight:409.25

1228551-75-4 Synthesis

1H-Pyrrolo[2,3-b]pyridine-3-carboxylic acid, 5-broMo-2-Methyl-, Methyl ester

1228551-75-4
10 suppliers
inquiry

98-09-9
339 suppliers
$12.00/25g

1H-Pyrrolo[2,3-b]pyridine-3-carboxylic acid, 5-broMo-2-Methyl-1-(phenylsulfonyl)-, Methyl ester

1200130-72-8
1 suppliers
inquiry

Yield:1200130-72-8 94%

Reaction Conditions:

with N-benzyl-N,N,N-triethylammonium chloride;sodium hydroxide in dichloromethane at 0 - 20; for 1.33333 h;

Steps:

Step 5 : l-Benzenesulfonyl-5-bromo-2-methyl-lH-pyrrolor2,3-blpyridine-3-carboxylic acid methyl esterA cooled (0-5 °C) suspension of 5-bromo-2-methyl-lH-pyrrolo[2,3-b]pyridine-3- carboxylic acid methyl ester (85 g, 316 mmol), powdered sodium hydroxide (38.1 g, 953mmol) and benzyltriethylammonium chloride (1.46 g, 6.3 mmol) in dichloromethane (1 L) was treated over ca. 5 minutes with benzenesulfonyl chloride (69.5 g, 51 mL, 394 mmol). The reaction mixture was allowed to stir at 0-5 °C for 15 minutes then allowed to warm to ambient temperature and stirred for 1 hour. The solid was removed by filtration through celite and the cake washed with dichloromethane. The filtrate was evaporated and the resultant residue triturated with diethyl ether to afford the title compound as a buff solid (122 g, 94%). 1H NMR (400 MHz, CDC1₃): 8.43 (d, J = 2.3 Hz, 1H), 8.40 (d, J = 2.3 Hz, 1H), 8.20-8.16 (m, 2H), 7.65-7.59 (m, 1H), 7.54-7.49 (m, 2H), 3.94 (s, 3H), 3.16 (s, 3H).

References:

WO2011/73263,2011,A1 Location in patent:Page/Page column 80