Benzenesulfonyl chloride → 1-benzenesulfonyl-5-methoxymethyl-1H-pyrrolo[2,3-b]pyridine

HRID 1515682Notes

Reaction equation

[CH3:1][O:2][CH2:3][C:4]1[CH:5]=[C:6]2[CH:12]=[CH:11][NH:10][C:7]2=[N:8][CH:9]=1.[OH-].[Na+].[C:15]1([S:21](Cl)(=[O:23])=[O:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl>[C:15]1([S:21]([N:10]2[C:7]3=[N:8][CH:9]=[C:4]([CH2:3][O:2][CH3:1])[CH:5]=[C:6]3[CH:12]=[CH:11]2)(=[O:23])=[O:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of tetrabutylammonium bromide (104 mg, 0.32 mmol) and 5-methoxymethyl-1H-pyrrolo[2,3-b]pyridine (1.74 g, 10.76 mmol) in dichloromethane (100 mL) was added sodium hydroxide powder (1.3 g, 32.4 mmol) at 0° C. The mixture was stirred at 0° C. for 5 min and then treated with benzene sulfonyl chloride (1.7 mL, 14.0 mmol). The mixture was stirred at 0° C. for another 15 min before it was warmed to 25° C. and stirred for 12 h. The resulting mixture was filtered and then concentrated in vacuo. Purification by flash silica gel chromatography (silica gel from QingDao, 200-300 mesh, glass column from Shanghai SD company, 25% ethyl acetate/hexanes) afforded 1-benzenesulfonyl-5-methoxymethyl-1H-pyrrolo[2,3-b]pyridine (1.54 g, 47.5%) as a white solid: LC/MS m/e calcd for C15H14N2O3S [M+H]+ 303.35, observed 302.9.

Workup

stirringThe mixture was stirred at 0° C. for another 15 min before it
temperaturewas warmed to 25° C.
stirringstirred for 12 h
filtrationThe resulting mixture was filtered
concentrationconcentrated in vacuo
customPurification by flash silica gel chromatography (silica gel from QingDao, 200-300 mesh, glass column from Shanghai SD company, 25% ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-3b32470ce88e4ef09bd0a6dc32046745
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08222416B2

Reaction notes

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