Benzenesulfonyl chloride → 1-(Benzenesulfonyl)-5-bromo-1H-pyrrolo[2,3-b]pyridine

HRID 1515601Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

Sodium hydroxide (4.1 g, 102.8 mmol) was added to a solution of tetrabutylammonium bromide (331 mg, 1.0 mmol) and 5-bromo-1H-pyrrolo[2,3-b]pyridine (6.7 g, 34.7 mmol) in dichloromethane (80 mL) at 0° C. The mixture was stirred at 0° C. for 5 min. Benzene sulfonyl chloride (5.7 mL, 44.5 mmol) was added to the above mixture slowly at 0° C. The resulting mixture was stirred at 0° C. for 15 min before it was warmed to 25° C. and kept stirring at that temperature for 12 h. The reaction mixture was filtered and the filtrate was concentrated in vacuo and then washed with hexanes to afford 1-benzenesulfonyl-5-bromo-1H-pyrrolo[2,3-b]pyridine as a white solid (11.8 g, 100%): LC/MS m/e calcd for C13H10BrN2O2S [M+H]+ 338.20, observed 337.1, 339.1; 1H NMR (400 MHz, CDCl3) δ ppm 6.56 (d, J=4.0 Hz, 1H), 7.51 (m, 2H), 7.60 (m, 1H), 7.75 (d, J=4.0 Hz, 1H), 7.98 (d, J=2.1 Hz, 1H), 8.18 (m, 2H), 8.45 (d, J=2.0 Hz, 1H).

Workup

stirringThe resulting mixture was stirred at 0° C. for 15 min before it
temperaturewas warmed to 25° C.
stirringkept stirring at that temperature for 12 h
filtrationThe reaction mixture was filtered
concentrationthe filtrate was concentrated in vacuo
washwashed with hexanes

Sources & evidence

ORD record: ord-93fd3deefdf446cd94131e67abbacfc5
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08222416B2

Reaction notes

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