Triethylamine → 4-Amino-3-(4-chlorophenoxy)-2-methyl-1H-indole-1-acetic acid, 1,1-dimethylethyl ester

HRID 2233743Notes

Reaction equation

HRID 2233743 reaction equation
[CH3:1][C:2]([O:5][C:6](=[O:30])[CH2:7][N:8]1[C:16]2[C:11](=[C:12]([N+:18]([O-])=O)[CH:13]=[CH:14][C:15]=2Br)[C:10]([O:21][C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)=[C:9]1[CH3:29])([CH3:4])[CH3:3].C(N(CC)CC)C>CCOC(C)=O.[Pt]>[NH2:18][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:11]=1[C:10]([O:21][C:22]1[CH:23]=[CH:24][C:25]([Cl:28])=[CH:26][CH:27]=1)=[C:9]([CH3:29])[N:8]2[CH2:7][C:6]([O:5][C:2]([CH3:3])([CH3:4])[CH3:1])=[O:30]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 686169457-Bromo-3-(4-chlorophenoxy)-2-methyl-4-nitro-1H-indole-1-acetic acid 1,1 dimethylethyl ester

Product 1

HCID 866092304-Amino-3-(4-chlorophenoxy)-2-methyl-1H-indole-1-acetic acid, 1,1-dimethylethyl ester

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the product from step (iii) (0.18 g) in EtOAc (30 ml) was added triethylamine (0.15 ml) and 5% Pt/C (36 mg) and the reaction stirred under hydrogen (1 atm) for 2 h. The reaction was filtered through celite and the filtrate evaporated under reduced pressure. Yield 0.139 g.

Workup

  1. filtrationThe reaction was filtered through celite
  2. customthe filtrate evaporated under reduced pressure

Sources & evidence

ORD record
ord-ed29568ca60e40dab39b8b97d8cce620
Source dataset
uspto-grants-2010_05
Patent number
US07709521B2

Reaction notes

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