Potassium Hydroxide → 1-[4-(trifluoromethyl)benzyl]-1H-indole-7-carboxylic Acid

HRID 1694382Notes

Reaction equation

HRID 1694382 reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]1[CH:22]=[CH:21][C:6]([CH2:7][N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[C:17]([O:19]C)=[O:18])[CH:10]=[CH:9]2)=[CH:5][CH:4]=1.[OH-].[K+]>C1COCC1.CO>[F:23][C:2]([F:1])([F:24])[C:3]1[CH:22]=[CH:21][C:6]([CH2:7][N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[C:17]([OH:19])=[O:18])[CH:10]=[CH:9]2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 57434482Methyl 1-[4-(trifluoromethyl)benzyl]-1H-indole-7-carboxylate

Product 1

HCID 510511811-[4-(trifluoromethyl)benzyl]-1H-indole-7-carboxylic Acid

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Methyl 1-[4-(trifluoromethyl)benzyl]-1H-indole-7-carboxylate (11.7 g, 35.1 mmol) was dissolved in 350 ml of 1:1 THF/MeOH and 175 ml of 2N KOH (10 eq, 351 mmol). The mixture was stirred at RT for 18 hr. Then the solvents were evaporated under reduced pressure. 2N HCl was added (pH=3) and the aqueous phase was extracted 3× with DCM. The combined organic layers were washed with water and brine, dried over MgSO4, filtered and then concentrated under reduced pressure. 1H NMR (500 MHz, DMSO-d6): δ 12.85 (bs, 1H), 7.80 (d, 1H), 7.60 (m, 3H), 7.50 (m, 1H), 7.10 (t, 1H), 7.00 (d, 2H), 6.70 (d, 1H), 5.80 (s, 2H).

Workup

  1. customThen the solvents were evaporated under reduced pressure
  2. addition2N HCl was added (pH=3)
  3. extractionthe aqueous phase was extracted 3× with DCM
  4. washThe combined organic layers were washed with water and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b00864012a3d476193d74d0887d2914f
Source dataset
uspto-grants-2012_04
Patent number
US08158671B2

Reaction notes

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