Water → HCID 67156018, compound

HRID 2196718Notes

Reaction equation

[CH:1]([N-]C(C)C)(C)C.[Li+].[CH3:9][C:10]1[C:18]2[C:13](=[N:14][CH:15]=[CH:16][CH:17]=2)[N:12]([S:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)(=[O:21])=[O:20])[CH:11]=1.CI.O>C1COCC1.ClCCl>[CH3:1][C:11]1[N:12]([S:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)(=[O:20])=[O:21])[C:13]2=[N:14][CH:15]=[CH:16][CH:17]=[C:18]2[C:10]=1[CH3:9]

Participants

Conditions

Temperature: -78 °C

Procedure

Lithium diisopropylamide (0.88 mL, 1.52 mmol, 1.8M in heptane/THF/ethylbenzene) was added to a solution of 3-methyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (0.20 g, 0.734 mmol) in THF (4.0 mL) at −78° C. The slurry was stirred at −78° C. for 30 minutes, and then methyl iodide (0.059 mL, 0.952 mmol) was added. The reaction mixture was allowed to warm up to room temperature and stirred for 2 hours. Water was then added to the mixture followed by dichloromethane. The layers were separated. The aqueous layer was extracted twice with dichloromethane. The organic layers were dried with sodium sulfate, filtered and concentrated in vacuo. The crude was purified by flash chromatography to afford 2,3-dimethyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (0.17 g, 99%) as a solid (purity 80%).

Workup

temperatureto warm up to room temperature
stirringstirred for 2 hours
customThe layers were separated
extractionThe aqueous layer was extracted twice with dichloromethane
dry with materialThe organic layers were dried with sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customThe crude was purified by flash chromatography

Sources & evidence

ORD record: ord-44d14ca77cee4a7eaf3b094693fe76da
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08338452B2

Reaction notes

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