Ethyl 5-[(phenylmethyl)oxy]-1-(2,2,2-trifluoroethyl)-1H-indole-2-carboxylate → Ethyl 5-hydroxy-1-(2,2,2-trifluoroethyl)-1H-indole-2-carboxylate

HRID 913386Notes

Reaction equation

HRID 913386 reaction equation
C1(C[O:8][C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[N:14]([CH2:18][C:19]([F:22])([F:21])[F:20])[C:13]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:12]3)C=CC=CC=1>[Pd]>[OH:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH2:18][C:19]([F:22])([F:20])[F:21])[C:13]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:12]2

Participants

3

Reactant 1

HCID 57800458Ethyl 5-[(phenylmethyl)oxy]-1-(2,2,2-trifluoroethyl)-1H-indole-2-carboxylate

Product 1

HCID 24985291Ethyl 5-hydroxy-1-(2,2,2-trifluoroethyl)-1H-indole-2-carboxylateYield 89%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a solution of ethyl 5-[(phenylmethyl)oxy]-1-(2,2,2-trifluoroethyl)-1H-indole-2-carboxylate (0.23 g, 0.6 mmol) in EtOAC (5 mL), under N2, was added 5% Pd/C (0.12 g). The mixture was hydrogenated under balloon pressure for 3 h. The catalyst was filtered off and washed with EtOAc. The filtrate was concentrated to afford the title compound (0.15 g, 89% yield): MS (ES) m/z 288 (M+1).

Workup

  1. filtrationThe catalyst was filtered off
  2. washwashed with EtOAc
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-70c51026c31d4b49b0107f650c0d698c
Source dataset
uspto-grants-2011_09
Patent number
US08026262B2

Reaction notes

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