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 537923

反応式

HRID 537923 の反応式
[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

参加物

5

反応物 3

HCID 2773516Methyl 2,3-dihydro-2-oxo-1H-indole-5-carboxylateHCID 126719604-Bromo-5,5-dimethylfuran-2-oneHCID 23714775LiHMDS tetrahydrofuran

生成物 1

HCID 58926238methyl (3E)-3-(4-bromo-5,5-dimethylfuran-2(5H)-ylidene)-2-oxoindoline-5-carboxylate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

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%.

後処理

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

出典と根拠

ORDレコード
ord-32f89d5eedfe4fae8141a5e08a1e7ba9
出典データセット
uspto-grants-2014_10
特許番号
US08865682B2

関連ノート

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