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 132812Notes

Reaction equation

HRID 132812 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:23][C:24]([F:27])([F:26])[F:25])[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([O:15]CC1C=CC=CC=1)=[CH:10][CH:9]=2)=[O:5])[CH3:2]>[Pd].C(OCC)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:23][C:24]([F:27])([F:25])[F:26])[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([OH:15])=[CH:10][CH:9]=2)=[O:5])[CH3:2]

Participants

4

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 83%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5-benzyloxy-1-(2,2,2-trifluoro-ethyl)-1H-indole-2-carboxylic acid ethyl ester (intermediate 1, step a, 13.6 g, 1.0 eq.) and palladium on activated charcoal (10% by weight, 1.15 g, 0.03 eq.) in ethyl acetate (700 mL), was vigorously stirred for 4 days at room temperature under an atmosphere of hydrogen (1 Atm). The solid was filtered off and washed with ethyl acetate. The filtrate was evaporated to dryness and purified on silica eluting with 1:4 cyclohexane/ethyl acetate to yield 8.6 g (83%) of the desired product as white solid. MS (m/e): 288.5 (MH+, 100%).

Workup

  1. filtrationThe solid was filtered off
  2. washwashed with ethyl acetate
  3. customThe filtrate was evaporated to dryness
  4. custompurified on silica eluting with 1:4 cyclohexane/ethyl acetate

Sources & evidence

ORD record
ord-ca900537f43b462487773e29afded047
Source dataset
uspto-grants-2008_06
Patent number
US07388095B2

Reaction notes

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