Methyl 2,3-dihydro-2-oxo-1H-indole-5-carboxylate → methyl (3E)-3-(4-bromo-5,5-dimethylfuran-2(5H)-ylidene)-2-oxoindoline-5-carboxylate

HRID 2196147Notes

Reaction equation

[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([O:12][CH3:13])=[O:11])=[CH:7][CH:8]=2)[CH2:3][C:2]1=[O:14].[Br:15][C:16]1[C:20]([CH3:22])([CH3:21])[O:19][C:18](=O)[CH:17]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.C1COCC1>C1COCC1>[Br:15][C:16]1[C:20]([CH3:22])([CH3:21])[O:19]/[C:18](=[C:3]2/[C:2](=[O:14])[NH:1][C:9]3[C:4]/2=[CH:5][C:6]([C:10]([O:12][CH3:13])=[O:11])=[CH:7][CH:8]=3)/[CH:17]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a 0° C. stirred solution of methyl oxindole-5-carboxylate (421 mg, 2.2 mmol) and 4-bromo-5,5-dimethylfuran-2(5H)-one (382 mg, 2.0 mmol) in THF (10 mL), was added 1M LiHMDS/THF solution (4.4 mL, 4.4 mmol) under nitrogen. The mixture was stirred at 0° C. for 80 min, quenched with 2.5M H2SO4 (3 mL), and poured into 100 mL of water. The precipitates were filtered, washed with water, and dried in vacuo to give methyl (3E)-3-(4-bromo-5,5-dimethylfuran-2(5H)-ylidene)-2-oxoindoline-5-carboxylate as yellow solid. Yield: 408 mg, 56%.

Workup

customquenched with 2.5M H2SO4 (3 mL)
additionpoured into 100 mL of water
filtrationThe precipitates were filtered
washwashed with water
customdried in vacuo

Sources & evidence

ORD record: ord-06678239562545a4bb4a68eee795c5d2
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08338415B2

Reaction notes

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