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

HRID 1006275Notes

Reaction equation

HRID 1006275 reaction equation
[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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 131709914Lindlars catalystCatalystHCID 702EthanolSolvent

Procedure

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).

Workup

  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%)

Sources & evidence

ORD record
ord-2dd0859076c34bb08df8cfd364fcd101
Source dataset
uspto-grants-2004_09
Patent number
US06787651B2

Reaction notes

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