Sodium hydride → HCID 17723881, compound

HRID 571198Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[C:6]2=[O:13].[H-].[Na+].Br[CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19]>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:7](=[O:12])[C:6]2=[O:13]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 5-methoxyindoline-2,3-dione (0.5 g, 2.82 mmol) in dry DMF (7 ml), under nitrogen atmosphere, was cooled to 0° C., and sodium hydride (60% w/w dispersion in mineral oil, 0.135 g, 3.39 mmol) was added portionwise. The mixture was stirred at 0° C. for 1 hour, and tert-butyl 2-bromoacetate (0.458 ml, 3.10 mmol) was added dropwise. The reaction was then stirred at room temperature overnight. The solvent was evaporated, ethyl acetate was added, and the mixture was washed with brine. The organic layer was dried over Na2SO4, filtered and evaporated. The crude was purified by flash chromatography on silica gel (ethyl acetate:petroleum ether=8:2) to afford tert-butyl 2-(5-methoxy-2,3-dioxoindolin-1-yl)acetate (0.650 g, 2.231 mmol, 79% yield). MS/ESI+ 235.8 [MH-tert-Bu]+.

Workup

stirringThe reaction was then stirred at room temperature overnight
customThe solvent was evaporated
additionethyl acetate was added
washthe mixture was washed with brine
dry with materialThe organic layer was dried over Na2SO4
filtrationfiltered
customevaporated
customThe crude was purified by flash chromatography on silica gel (ethyl acetate:petroleum ether=8:2)

Sources & evidence

ORD record: ord-3893a2d57d2e408baca46c39d49aee49
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09024027B2

Reaction notes

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