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

HRID 1929163Notes

Reaction equation

HRID 1929163 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](F)[CH:19]=[C:18](F)[C:17]=1[N+:24]([O-])=O)[CH:11]=[CH:10][CH:9]=2)=[O:5])[CH3:2].[CH2:27](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]=[CH:20][C:19]([CH3:27])=[CH:18][C:17]=1[NH2:24])[CH:11]=[CH:10][CH:9]=2)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 702EthanolHCID 668421024-(3,5-Difluoro-2-nitro-phenoxy)-1H-indole-2-carboxylic acid ethyl ester

Product 1

HCID 668420484-(2-Amino-4-methyl-phenoxy)-1H-indole-2-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

138 (570 mg, 1.675 mmol) is dissolved in 150 ml of ethanol and, after addition of Pd—C (200 mg), the mixture is hydrogenated at room temperature for 2 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-fea9ad9292444ab28ca1dd7814955821
Source dataset
uspto-grants-2012_05
Patent number
US08183366B2

Reaction notes

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