Ethyl 3-(cyclopropylidenemethyl)-1-[3-(trifluoromethyl)benzyl]-1H-indole-2-carboxylate → Ethyl 3-(cyclopropylmethyl)-1-[3-(trifluoromethyl)benzyl]-1H-indole-2-carboxylate

HRID 1006275

反応式

HRID 1006275 の反応式
[C:1]1(=[CH:4][C:5]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[N:7]([CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=3)[C:6]=2[C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:3][CH2:2]1.[H][H]>[Pd].CC([O-])=O.CC([O-])=O.[Pb+2].C(O)C>[CH:1]1([CH2:4][C:5]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[N:7]([CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:23])([F:24])[F:22])[CH:16]=3)[C:6]=2[C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:3][CH2:2]1

参加物

5

反応物 2

HCID 22676741Ethyl 3-(cyclopropylidenemethyl)-1-[3-(trifluoromethyl)benzyl]-1H-indole-2-carboxylateHCID 178418361HCID 178418361、化合物

生成物 1

HCID 22676804Ethyl 3-(cyclopropylmethyl)-1-[3-(trifluoromethyl)benzyl]-1H-indole-2-carboxylate

試薬・触媒・溶媒 2

HCID 131709914Lindlars catalyst触媒HCID 702Ethanol溶媒

実験手順

Ethyl 3-(cyclopropylidenemethyl)-1-[3-(trifluoromethyl)benzyl]-1H-indole-2-carboxylate (Example 182, 140 mg, 0.351 mmol) was stirred over Lindlar catalyst (28 mg) in ethanol (15 mL) under 1 atmosphere of hydrogen for 1 hour. The mixture was filtered through Celite with an excess of ethanol. The filtrate was concentrated, and the resulting crude oil was purified by flash chromatography on silica gel eluted with 20% Et2O/hexane. The title compound was collected as a yellow oil (95 mg, 67%). The product had: 1H NMR (300 MHz, acetone-d6) δ 7.78 (d, 1 H), 7.56-7.45 (m, 4 H), 7.34-7.32 (m, 1 H), 7.28-7.26 (m, 1 H), 7.16-7.13 (m, 1 H), 5.93 (s, 2 H), 4.32 (q, 2 H), 3.08 (d, 2 H), 1.31 (t, 3 H), 1.13-1.15 (m, 1 H), 0.42-0.38 (m, 2 H), 0.29-0.26 (m, 2 H).

後処理

  1. filtrationThe mixture was filtered through Celite with an excess of ethanol
  2. concentrationThe filtrate was concentrated
  3. customthe resulting crude oil was purified by flash chromatography on silica gel
  4. washeluted with 20% Et2O/hexane
  5. customThe title compound was collected as a yellow oil (95 mg, 67%)

出典と根拠

ORDレコード
ord-2dd0859076c34bb08df8cfd364fcd101
出典データセット
uspto-grants-2004_09
特許番号
US06787651B2

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