Potassium Hydroxide → HCID 60026523, compound

HRID 400694Notes

Reaction equation

HRID 400694 reaction equation
C([O:3][C:4]([C:6]1[C:7]2[CH:8]=[C:9]([CH2:15][C:16]([OH:34])([C:30]([F:33])([F:32])[F:31])[CH2:17][C:18]([C:21]3[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:22]=3[O:28][CH3:29])([CH3:20])[CH3:19])[NH:10][C:11]=2[CH:12]=[CH:13][CH:14]=1)=[O:5])C.[OH-].[K+]>CO.O>[F:27][C:25]1[CH:24]=[CH:23][C:22]([O:28][CH3:29])=[C:21]([C:18]([CH3:19])([CH3:20])[CH2:17][C:16]([OH:34])([C:30]([F:32])([F:33])[F:31])[CH2:15][C:9]2[NH:10][C:11]3[CH:12]=[CH:13][CH:14]=[C:6]([C:4]([OH:5])=[O:3])[C:7]=3[CH:8]=2)[CH:26]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 60026778HCID 60026778, compound

Product 1

HCID 60026523HCID 60026523, compoundYield 89.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 2-[4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-trifluoromethylpentyl]-1H-indole-4-carboxylic acid ethyl ester (220 mg, 0.470 mmol) in 10 mL of methanol was treated with a solution of potassium hydroxide (85 mg, 1.5 mmol) in 3 mL of water. The resulting mixture was stirred at room temperature for 4 hours, refluxed for 6 hours, cooled to room temperature, and concentrated in vacuo. The residue was treated with cold 1 N sulfuric acid and extracted with three 30 mL portions of dichloromethane. The combined organic layers were washed with water, dried over sodium sulfate, filtered, and concentrated in vacuo to give 190 mg of the title product as a light cream solid (89% yield).

Workup

  1. temperaturerefluxed for 6 hours
  2. temperaturecooled to room temperature
  3. concentrationconcentrated in vacuo
  4. additionThe residue was treated with cold 1 N sulfuric acid
  5. extractionextracted with three 30 mL portions of dichloromethane
  6. washThe combined organic layers were washed with water
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-de53a11b8418444dafea4caecb0e79ff
Source dataset
uspto-grants-2014_06
Patent number
US08741897B2

Reaction notes

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