Sodium Hydroxide → HCID 22497225, compound

HRID 1816093Notes

Reaction equation

HRID 1816093 reaction equation
FC(F)(F)[C:3]([C:5]1[C:13]2[C:8](=[CH:9][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:11][CH:12]=2)[N:7]([CH:18]([CH3:20])[CH3:19])[CH:6]=1)=[O:4].[OH-:23].[Na+]>>[CH:18]([N:7]1[C:8]2[C:13](=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)[C:5]([C:3]([OH:4])=[O:23])=[CH:6]1)([CH3:20])[CH3:19]

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 22497250HCID 22497250, compound

Product 1

HCID 22497225HCID 22497225, compoundYield 99%

Conditions

Temperature
25 °C

Procedure

A solution of 2,2,2-trifluoro-1-(1-isopropyl-6-trifluoromethyl-1H-indol-3-yl)-ethanone (800 mg, 2.48 mmol) in a 20% aqueous sodium hydroxide solution (12 mL) was heated at 110° C. for 3 h. At this time, the reaction was cooled to 25° C., partitioned between water (100 mL) and ethyl acetate (100 mL), and treated with a 1N aqueous hydrochloric acid solution (50 mL). The organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo to afford 1-isopropyl-6-trifluoromethyl-1H-indole-3-carboxylic acid (704 mg, 99%) as a yellow solid: mp 177-178° C.; EI-HRMS m/e calcd for C13H12F3NO2 (M+) 271.0820, found 271.0807.

Workup

  1. custompartitioned between water (100 mL) and ethyl acetate (100 mL)
  2. additiontreated with a 1N aqueous hydrochloric acid solution (50 mL)
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-73b4121010da4e06a9bd3762dbd97ae9
Source dataset
uspto-grants-2005_04
Patent number
US06881844B2

Reaction notes

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