Lithium Hydroxide → 3-bromo-1H-indole-2-carboxylic acid

HRID 1874794Notes

Reaction equation

HRID 1874794 reaction equation
[Br:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]=1[C:11]([O:13]CC)=[O:12].[OH-].[Li+]>C1COCC1.CO.O>[Br:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]=1[C:11]([OH:13])=[O:12]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 4715017Ethyl 3-Bromoindole-2-carboxylate

Product 1

HCID 23256883-bromo-1H-indole-2-carboxylic acidYield 67%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Ethyl 3-bromo-1H-indole-2-carboxylate (0.070 g, 0.30 mmol) and powdered lithium hydroxide (0.073 g, 3.0 mmol) were dissolved in 1:1:1 mixture of THF/MeOH/water (3.0 mL) and the solution was stirred at RT for 4.5 h. The solvent was evaporated. Purification was accomplished by Reverse-Phase HPLC (water/acetonitrile with 0.1% TFA) to afford (0.042 g, 67%) of the title compound as a white solid. 1H NMR (400 MHz, DMSO-d6): δ ppm 12.09 (br. s., 1H), 7.50 (d, 1H), 7.43 (d, 1H), 7.30 (t, 1H), 7.15 (t, 1H). MS: m/z 240.1 (M+1).

Workup

  1. customThe solvent was evaporated
  2. customPurification

Sources & evidence

ORD record
ord-d27e492da8ce479a8d2419628b7c2b93
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

Loading…