Methanol → 3-bromo-5-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-1H-indole-2-carboxylic acid

HRID 1875039Notes

Reaction equation

HRID 1875039 reaction equation
[OH-].[Li+].[Br:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:11]=2)[NH:6][C:5]=1[C:21]([O:23]CC)=[O:22].CO.O>C1COCC1>[Br:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:18])[CH3:19])=[O:15])[CH:11]=2)[NH:6][C:5]=1[C:21]([OH:23])=[O:22]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 3939Lithium HydroxideHCID 68484480Ethyl 3-bromo-5-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-1H-indole-2-carboxylate

Product 1

HCID 684865673-bromo-5-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-1H-indole-2-carboxylic acidYield 90.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide (0.113 g, 4.72 mmol) was added to a solution of ethyl 3-bromo-5-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-1H-indole-2-carboxylate (0.181 g, 0.472 mmol) in THF:methanol:water/3:1:1 (5 mL). The mixture was stirred at room temperature overnight. The solvent was evaporated and the residue was taken up in water, acidified with 1 N aqueous HCl and extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated to give the title compound (0.151 g, 77%) as a beige solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.81 (br. s., 1H), 9.27 (br. s., 1H), 7.73 (br. s., 1H), 7.22-7.33 (m, 2H), 1.44-1.54 (m, 9H).

Workup

  1. customThe solvent was evaporated
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-7dfcc1c0e0304cff92e81d4fc7a64a0c
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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