Benzenesulfonyl chloride → 3-Bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

HRID 2196701Notes

Reaction equation

[H-].[Na+].[Br:3][C:4]1[C:12]2[C:7](=[N:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.[C:13]1([S:19](Cl)(=[O:21])=[O:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CN(C=O)C>[Br:3][C:4]1[C:12]2[C:7](=[N:8][CH:9]=[CH:10][CH:11]=2)[N:6]([S:19]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)(=[O:21])=[O:20])[CH:5]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Sodium hydride (2.13 g, 53.3 mmol, 60% dispersion in mineral oil) was added to 3-bromo-1H-pyrrolo[2,3-b]pyridine (7.5 g, 38.1 mmol) in DMF (190 mL) at 0° C. This mixture was stirred at 0° C. for 30 minutes, and benzene sulfonyl chloride (7.40 g, 41.87 mmol) was then added by syringe. After 30 minutes at 0° C., TLC indicated most of the starting material had been consumed. Benzene sulfonyl chloride (0.5 mL) was added, and the mixture was stirred for another 15 minutes at 0° C. The mixture was then quenched with saturated ammonium chloride solution (100 mL) followed by water (200 mL). A precipitate had formed. The solids were collected by filtration and dried under high vacuum for 16 hours to give 3-bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (11.2 g, 87%) as a solid. 1H NMR (400 MHz, CDCl3) δ 8.46-8.49 (m, 1H), 8.19-8.22 (m, 2H), 7.79-7.83 (m, 2H), 7.57-7.62 (m, 1H), 7.47-7.53 (m, 2H), 7.25-7.29 (m, 1H).

Workup

waitAfter 30 minutes at 0° C.
customhad been consumed
additionBenzene sulfonyl chloride (0.5 mL) was added
stirringthe mixture was stirred for another 15 minutes at 0° C
customThe mixture was then quenched with saturated ammonium chloride solution (100 mL)
customA precipitate had formed
filtrationThe solids were collected by filtration
customdried under high vacuum for 16 hours

Sources & evidence

ORD record: ord-b8a192c8b8fb4a3eb46f0b9a12a07f7d
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08338452B2

Reaction notes

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