Methyl iodide → 6-bromo-3,3-dimethyl-2,3-dihydro-1H-indol-2-one

To a suspension of potassium tert-butylate (12.8 g, 114 mmol) in dry THF (80 ml) at 0° C. under an argon atmosphere was added portionwise 6-bromoindolin-2-one (5.0 g, 22.9 mmol) followed by copper(I) bromide-dimethylsulfide complex (470 mg, 2.29 mmol). MeI (6.82 g, 3.00 ml, 48.0 mmol) was added dropwise within 45 minutes, keeping temperature of the reaction mixture below 8° C. The reaction mixture was warmed to room temperature and kept at this temperature for 16 hours. The reaction mixture was cooled to 0° C. again and saturated aqueous ammonium chloride solution was cautiously added. The mixture was diluted with tert-butyl methyl ether and water. The aqueous phase was extracted with tert-butyl methyl ether, the combined organic phases were dried over sodium sulfate, the solvent was evaporated and the residue purified by silica gel chromatography using ethyl acetate/heptane as eluent. The title compound was obtained as light yellow solid (5.17 g).

1. customtemperature of the reaction mixture below 8° C
2. temperatureThe reaction mixture was cooled to 0° C. again
3. extractionThe aqueous phase was extracted with tert-butyl methyl ether
4. dry with materialthe combined organic phases were dried over sodium sulfate
5. customthe solvent was evaporated
6. customthe residue purified by silica gel chromatography

ORD 기록

ord-bd5fad5eede5496fb0f6954d13438288

출처 데이터셋

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US09221816B2