4-(5-Methyl-2-nitro-phenoxy)-1H-indole-2-carboxylic acid ethyl ester → 4-(2-Amino-5-methyl-phenoxy)-1H-indole-2-carboxylic acid ethyl ester

HRID 2267868Notes

Reaction equation

HRID 2267868 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[C:12]([O:15][C:16]1[CH:21]=[C:20]([CH3:22])[CH:19]=[CH:18][C:17]=1[N+:23]([O-])=O)[CH:11]=[CH:10][CH:9]=2)=[O:5])[CH3:2]>C(OCC)(=O)C.[Pd]>[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[C:12]([O:15][C:16]1[CH:21]=[C:20]([CH3:22])[CH:19]=[CH:18][C:17]=1[NH2:23])[CH:11]=[CH:10][CH:9]=2)=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 668413744-(5-Methyl-2-nitro-phenoxy)-1H-indole-2-carboxylic acid ethyl ester

Product 1

HCID 668415234-(2-Amino-5-methyl-phenoxy)-1H-indole-2-carboxylic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

134 (1.3 g, 3.82 mmol) is dissolved in 250 ml of ethyl acetate and, after addition of Pd—C (200 mg), the mixture is hydrogenated at room temperature for 3 hours. The mixture is filtrated over celite to remove the catalyst and evaporated.

Workup

  1. filtrationThe mixture is filtrated over celite
  2. customto remove the catalyst
  3. customevaporated

Sources & evidence

ORD record
ord-28d430b9d203432e8d9d0fe570a8f89b
Source dataset
uspto-grants-2010_12
Patent number
US07858781B2

Reaction notes

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