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

HRID 2196696Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

3-Bromo-1H-pyrrolo[2,3-b]pyridine (7.5 g, 38.07 mmol) was dissolved in dry DMF (190 mL) and chilled to 0° C. Sodium hydride (60% dispersion in mineral oil, 2.13 g, 53.29 mmol) was then added, and the mixture stirred at 0° C. for 30 minutes. Benzenesulfonyl chloride (7.41 g, 41.87 mmol) was then added via syringe and the mixture stirred at 0° C. for 30 minutes. Another lot of benzenesulfonyl chloride (0.5 mL) was then added to consume the starting material. The reaction mixture was then carefully quenched with saturated ammonium chloride, followed by water (200 mL) to precipitate the product. The solids were collected by filtration and dried under vacuum 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), 8.19-8.23 (m, 2H), 7.79-7.84 (m, 2H), 7.57-7.62 (m, 1H), 7.47-7.53 (m, 2H), 7.25-7.29 (m, 1H).

Workup

stirringthe mixture stirred at 0° C. for 30 minutes
customto consume the starting material
customThe reaction mixture was then carefully quenched with saturated ammonium chloride
customto precipitate the product
filtrationThe solids were collected by filtration
customdried under vacuum

Sources & evidence

ORD record: ord-cc2d08872a324ccca824526d356d9449
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08338452B2

Reaction notes

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