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

HRID 1515580Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[CH:13]=[CH:12][NH:11][C:8]2=[N:9][CH:10]=1)=[O:4].[OH-].[Na+].[C:16]1([S:22](Cl)(=[O:24])=[O:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[CH:13]=[CH:12][N:11]([S:22]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)(=[O:24])=[O:23])[C:8]2=[N:9][CH:10]=1)=[O:4]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of tetrabutylammonium bromide (154 mg, 0.48 mmol) and 1H-pyrrolo[2,3-b]pyridin-5-carboxylic acid methyl ester (2.8 g, 15.9 mmol) in dichloromethane (40 mL) was added sodium hydroxide powder (1.9 g, 47.7 mmol) at 0° C. The mixture was stirred at 0° C. for 5 min. Benzene sulfonyl chloride (3 mL, 23.8 mmol) was added slowly to the above mixture at 0° C. and the resulting mixture was stirred at 0° C. for another 15 min before it was warmed to 25° C. and kept at that temperature for 12 h. The reaction mixture was filtered and then concentrated in vacuo to afford 1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-5-carboxylic acid methyl ester as a light yellow solid which was washed with hexane to give a white solid (4.6 g, 90%): 1H NMR (400 MHz, CDCl3) δ ppm 3.95 (s, 3H), 6.69 (d, J=4.0 Hz, 1H), 7.51 (m, 2H), 7.61 (m, 1H), 7.82 (d, J=4.0 Hz, 1H), 8.22 (m, 2H), 8.51 (d, J=2.0 Hz, 1H), 9.08 (d, J=2.0 Hz, 1H).

Workup

stirringthe resulting mixture was stirred at 0° C. for another 15 min before it
temperaturewas warmed to 25° C.
waitkept at that temperature for 12 h
filtrationThe reaction mixture was filtered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-7e3627203e4e44c7b8ebc6a2d7c8490a
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08222416B2

Reaction notes

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