Sodium Hydroxide → 6-bromo-1-isopropyl-1H-indole-3-carboxylic acid

HRID 1816117Notes

Reaction equation

HRID 1816117 reaction equation
FC(F)(F)[C:3]([C:5]1[C:13]2[C:8](=[CH:9][C:10]([Br:14])=[CH:11][CH:12]=2)[N:7]([CH:15]([CH3:17])[CH3:16])[CH:6]=1)=[O:4].[OH-:20].[Na+]>>[Br:14][C:10]1[CH:9]=[C:8]2[C:13]([C:5]([C:3]([OH:4])=[O:20])=[CH:6][N:7]2[CH:15]([CH3:17])[CH3:16])=[CH:12][CH:11]=1

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 224972312,2,2-trifluoro-1-(6-bromo-1-isopropyl-1H-indol-3-yl)-ethanone

Product 1

HCID 224972346-bromo-1-isopropyl-1H-indole-3-carboxylic acidYield 94%

Conditions

Temperature
25 °C

Procedure

A solution of 2,2,2-trifluoro-1-(6-bromo-1-isopropyl-1H-indol-3-yl)-ethanone (3.30 g, 9.88 mmol) in a 20% aqueous sodium hydroxide solution (35 mL) was heated at 110° C. for 18 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 (60 mL). The organic layer was then washed with a saturated aqueous sodium chloride solution (1×100 mL), dried over magnesium sulfate, filtered, and concentrated in vacuo to afford 6-bromo-1-isopropyl-1H-indole-3-carboxylic acid (2.63 g, 94%) as a yellow solid: mp 207-209° C.; EI-HRMS m/e calcd for C12H12BrNO2 (M+) 281.0051, found 281.0047.

Workup

  1. custompartitioned between water (100 mL) and ethyl acetate (100 mL)
  2. additiontreated with a 1N aqueous hydrochloric acid solution (60 mL)
  3. washThe organic layer was then washed with a saturated aqueous sodium chloride solution (1×100 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2941f1548046418cacc43fcd2fa6b6a8
Source dataset
uspto-grants-2005_04
Patent number
US06881844B2

Reaction notes

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