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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
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HRID 2215787 반응식
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
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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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
55 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-cdb94898369d42dba552c7dae3a48114
출처 데이터셋
uspto-grants-2006_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07109229B2

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