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 383496

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-b0204de75f414848aed1d1e509ad7d62
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367664B2

Linked notes

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