Water → HCID 67155777, compound

HRID 2196722Notes

Reaction equation

C([N-]C(C)C)(C)C.[Li+].[C:9]1([S:15]([N:18]2[C:22]3=[N:23][CH:24]=[CH:25][CH:26]=[C:21]3[CH:20]=[CH:19]2)(=[O:17])=[O:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[C:27](OC(=O)C)(=[O:29])[CH3:28].O>C1COCC1.ClCCl>[C:9]1([S:15]([N:18]2[C:22]3=[N:23][CH:24]=[CH:25][CH:26]=[C:21]3[CH:20]=[C:19]2[C:27](=[O:29])[CH3:28])(=[O:17])=[O:16])[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

Conditions

Temperature: -78 °C

Procedure

Lithium diisopropylamide (19.4 mL, 35.0 mmol, 1.8M in heptane/THF/ethylbenzene) was added to a solution of 1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (4.50 g, 17.4 mmol) in THF (100 mL) at −78° C. The reaction mixture was stirred at −78° C. for 30 minutes, and then acetic anhydride (6.6 mL, 69.7 mmol) was added. The reaction mixture was warmed up to room temperature and stirred for 40 minutes. The reaction mixture was treated with water and dichloromethane, and the layers were separated. The aqueous layer was extracted once with dichloromethane. The organic layers were dried with sodium sulfate, filtered and concentrated in vacuo. The crude material was purified by flash chromatography to afford 1-(1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl)ethanone (2.15 g, 41%).

Workup

temperatureThe reaction mixture was warmed up to room temperature
stirringstirred for 40 minutes
customthe layers were separated
extractionThe aqueous layer was extracted once with dichloromethane
dry with materialThe organic layers were dried with sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customThe crude material was purified by flash chromatography

Sources & evidence

ORD record: ord-4d53b1d32896473eb2c31036a89ebebc
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08338452B2

Reaction notes

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