Water → 1-(1-tosyl-1H-pyrrolo[3,2-c]pyridin-4-yl)ethanone

HRID 2409010Notes

Reaction equation

[NH:1]1[C:9]2[CH:8]=[CH:7][N:6]=[C:5]([C:10](=[O:12])[CH3:11])[C:4]=2[CH:3]=[CH:2]1.[H-].[Na+].[CH3:15][C:16]1[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1.O>C1COCC1>[S:22]([N:1]1[C:9]2[CH:8]=[CH:7][N:6]=[C:5]([C:10](=[O:12])[CH3:11])[C:4]=2[CH:3]=[CH:2]1)([C:19]1[CH:20]=[CH:21][C:16]([CH3:15])=[CH:17][CH:18]=1)(=[O:24])=[O:23]

Participants

Conditions

Temperature: 0 °C

Procedure

To a mixture of 1-(1H-pyrrolo[3,2-c]pyridin-4-yl)ethanone (680 mg, 4.25 mmol) in anhydrous THF (40 mL) at 0° C. was added NaH (60% in mineral oil, 204 mg, 5.1 mmol). After the mixture was stirred at 0° C. for 30 min, 4-methylbenzene-1-sulfonyl chloride (850 mg, 4.46 mmol) was added. The reaction mixture was stirred at 0° C. for 1 h. The reaction mixture was poured into water (150 mL), extracted with EtOAc (3×50 mL) and concentrated under reduced pressure to afford 1.32 g (98.9%) of 1-(1-tosyl-1H-pyrrolo[3,2-c]pyridin-4-yl)ethanone as yellow solid: MS (ESI) m/z: 315.2 [M+1]+.

Workup

stirringThe reaction mixture was stirred at 0° C. for 1 h
extractionextracted with EtOAc (3×50 mL)
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-6251e424a08547b5bc31d43b22395dbb
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815877B2

Reaction notes

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