HCID 24805097, compound → 5-amino-1-benzyl-2-methyl-1H-indole-3-carboxylic acid, 3,4-difluorobenzylamide

HRID 16630Notes

Reaction equation

HRID 16630 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:29]=[CH:30][C:31]=1[F:32])[CH2:5][NH:6][C:7]([C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([N+:18]([O-])=O)[CH:16]=2)[N:11]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:10]=1[CH3:28])=[O:8]>CO.CCOC(C)=O.[Pd]>[F:1][C:2]1[CH:3]=[C:4]([CH:29]=[CH:30][C:31]=1[F:32])[CH2:5][NH:6][C:7]([C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([NH2:18])[CH:16]=2)[N:11]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:10]=1[CH3:28])=[O:8]

Participants

5

Reactant 1

HCID 24805097HCID 24805097, compound2×

Product 1

HCID 248050985-amino-1-benzyl-2-methyl-1H-indole-3-carboxylic acid, 3,4-difluorobenzylamideYield 104.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-benzyl-2-methyl-5-nitro-1H-indole-3-carboxylic acid, 3,4-difluorobenzylamide (Compound 45, 97 mg, 0.22 mmol) in MeOH (20 ml) and EtOAc (20 ml) was added Pd—C (10%, 47 mg, 0.045 mmol). The reaction was stirred under hydrogen for 24 h, filtered through Celite, washed with MeOH-EtOAc (1:1) to yield 5-amino-1-benzyl-2-methyl-1H-indole-3-carboxylic acid, 3,4-difluorobenzylamide (Compound 46) as a white solid (93 mg, 100%).

Workup

  1. filtrationfiltered through Celite
  2. washwashed with MeOH-EtOAc (1:1)

Sources & evidence

ORD record
ord-4fb188ab983c465d93cadba5da01ecf8
Source dataset
uspto-grants-2010_06
Patent number
US07737173B2

Reaction notes

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