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Tetrahydrofuran → 3-(1,5-dimethyl-1H-indol-7-yl)-4-(6-trifluoromethyl-1H-indol-3-yl)-pyrrole-2,5-dione

HRID 2215787
ノート
印刷プレビュー

反応式

HRID 2215787 の反応式
CO[C:3](=[O:17])[C:4]([C:6]1[CH:7]=[C:8]([CH3:16])[CH:9]=[C:10]2[C:14]=1[N:13]([CH3:15])[CH:12]=[CH:11]2)=O.[F:18][C:19]([F:34])([F:33])[C:20]1[CH:28]=[C:27]2[C:23]([C:24]([CH2:29][C:30]([NH2:32])=[O:31])=[CH:25][NH:26]2)=[CH:22][CH:21]=1.CC(C)([O-])C.[K+].C1COCC1>CN(C=O)C>[CH3:15][N:13]1[C:14]2[C:10](=[CH:9][C:8]([CH3:16])=[CH:7][C:6]=2[C:4]2[C:3](=[O:17])[NH:32][C:30](=[O:31])[C:29]=2[C:24]2[C:23]3[C:27](=[CH:28][C:20]([C:19]([F:18])([F:33])[F:34])=[CH:21][CH:22]=3)[NH:26][CH:25]=2)[CH:11]=[CH:12]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 8028TetrahydrofuranHCID 219500606-trifluoromethyl-1H-indol-3-yl-acetamideHCID 23665647Potassium tert-butoxideHCID 69642519(1,5-dimethyl-1H-indol-7-yl)-oxo-acetic acid methyl ester

生成物 1

HCID 219500643-(1,5-dimethyl-1H-indol-7-yl)-4-(6-trifluoromethyl-1H-indol-3-yl)-pyrrole-2,5-dione収率 60.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
55 °C

実験手順

To a mixture of (1,5-dimethyl-1H-indol-7-yl)-oxo-acetic acid methyl ester (0.40 g, 1.73 mmol) and 2-(6-trifluoromethyl-1H-indol-3-yl-acetamide (0.38 g, 1.57 mmol) in DMF (10 mL) was added absolution of potassium tert-butoxide in THF (1.0 M, 6.3 mL, 6.3 mmol) at room temperature. The reaction mixture was heated at 55° C. for 19 h, cooled to room temperature, and quenched with hydrochloric acid (1.0 N). After stirring at room temperature for 30 min, the mixture was extracted with ethyl acetate and the extract washed with water, saturated aqueous sodium bicarbonate and brine dried (sodium sulfate), filtered and evaporated. Flash column chromatography on silica gel eluting with chloroform and acetone gave 3-(1,5-dimethyl-1H-indol-7-yl)-4-(6-trifluoromethyl-1H-indol-3-yl)-pyrrole-2,5-dione (400 mg, 60.2%). 1HNMR (d6-DMSO, 400 MHz) 2.26 (s, 3H), 3.58 (s, 3H), 6.36 (d, J=3.2 Hz, 1H), 6.71 (d, J=8.4 Hz, 1H), 6.76 (d, J=1.2 Hz, 1H), 6.83 (d, J=8.0 Hz, 1H), 7.17 (d, J=3.2 Hz, 1H), 7.40 (s, 1H), 7.68 (s, 1H), 7.96 (d, J=2.8 Hz, 1H), 11.21 (s, 1H), 12.13 (s, 1H); MS (ES, m/z): C23H16F3N3O2: 424.13 (M++1): 422.23 (M+−1).

後処理

  1. temperaturecooled to room temperature
  2. customquenched with hydrochloric acid (1.0 N)
  3. extractionthe mixture was extracted with ethyl acetate
  4. washthe extract washed with water, saturated aqueous sodium bicarbonate and brine
  5. dry with materialdried (sodium sulfate)
  6. filtrationfiltered
  7. customevaporated

出典と根拠

ORDレコード
ord-cdb94898369d42dba552c7dae3a48114
出典データセット
uspto-grants-2006_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07109229B2

反応ノート

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