4-(4-Fluoro-2-nitro-phenoxy)-1H-indole-2-carboxylic acid ethyl ester → 4-(2-Amino-4-fluoro-phenoxy)-1H-indole-2-carboxylic acid ethyl ester

HRID 2267883Notes

Reaction equation

HRID 2267883 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]=[CH:20][C:19]([F:22])=[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]=[CH:20][C:19]([F:22])=[CH:18][C:17]=1[NH2:23])[CH:11]=[CH:10][CH:9]=2)=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 668417904-(4-Fluoro-2-nitro-phenoxy)-1H-indole-2-carboxylic acid ethyl ester

Product 1

HCID 668415214-(2-Amino-4-fluoro-phenoxy)-1H-indole-2-carboxylic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

146 (1.5 g, 4.21 mmol) is dissolved in 200 ml of ethyl acetate 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-cc1217bd526a4557b5d45708e2e787e8
Source dataset
uspto-grants-2010_12
Patent number
US07858781B2

Reaction notes

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