Benzenesulfonyl chloride → 4-Bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-B]pyridine

HRID 331007Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 4-bromo-1H-pyrrolo[2,3-b]pyridine (2 g, 10.15 mmol) in DMF (50 mL) stirred at 0° C. was added sodium hydride (0.487 g, 12.18 mmol). After stirring for 30 min at 0° C., benzenesulfonyl chloride (1.570 mL, 12.18 mmol) was added to the mixture and stirred at 0° C. for 1.5 hour. The reaction was quenched with addition of saturated NH4Cl aq. solution and the mixture was poured into saturated aq. NH4Cl (100 mL). The mixture was extracted with ethyl acetate (20 mL×3). The organic layers were combined, washed with brine (100 mL), dried over MgSO4, filtered and evaporated in vacuo. The residue was purified by chromatography on silica, eluting with a gradient of 0-25% ethyl acetate in cyclohexane to give the title compound (3.39 g). LCMS (A): m/z (M+H)+ 337/339, C13H9BrN2O2S requires 336/338 (acidic).

Workup

stirringstirred at 0° C. for 1.5 hour
customThe reaction was quenched with addition of saturated NH4Cl aq. solution
additionthe mixture was poured into saturated aq. NH4Cl (100 mL)
extractionThe mixture was extracted with ethyl acetate (20 mL×3)
washwashed with brine (100 mL)
dry with materialdried over MgSO4
filtrationfiltered
customevaporated in vacuo
customThe residue was purified by chromatography on silica
washeluting with a gradient of 0-25% ethyl acetate in cyclohexane

Sources & evidence

ORD record: ord-114d913268f249559ea375666939ecfd
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08877742B2

Reaction notes

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