4-(3,5-Difluoro-2-nitro-phenoxy)-1H-indole-2-carboxylic acid ethyl ester → 4-(2-Amino-3,5-difluoro-phenoxy)-1H-indole-2-carboxylic acid ethyl ester

HRID 2267893Notes

Reaction equation

HRID 2267893 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:22])[CH:19]=[C:18]([F:23])[C:17]=1[N+:24]([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]([F:22])[CH:19]=[C:18]([F:23])[C:17]=1[NH2:24])[CH:11]=[CH:10][CH:9]=2)=[O:5])[CH3:2]

Participants

4

Reactant 1

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

Product 1

HCID 668419064-(2-Amino-3,5-difluoro-phenoxy)-1H-indole-2-carboxylic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

154 (1.8 g, 4.87 mmol) is dissolved in 150 ml of ethyl acetate and, after addition of Pd—C (500 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-b95e4e5bfb0f41738eb31f6de82a0fc5
Source dataset
uspto-grants-2010_12
Patent number
US07858781B2

Reaction notes

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