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

HRID 1006275

반응식

HRID 1006275 반응식
[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

참가 물질

5

반응물 2

HCID 22676741Ethyl 3-(cyclopropylidenemethyl)-1-[3-(trifluoromethyl)benzyl]-1H-indole-2-carboxylateHCID 178418361HCID 178418361, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 131709914Lindlars catalyst촉매HCID 702Ethanol용매

실험 절차

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).

후처리

  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%)

출처 및 근거

ORD 기록
ord-2dd0859076c34bb08df8cfd364fcd101
출처 데이터셋
uspto-grants-2004_09
특허 번호
US06787651B2

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