HCID 59762312, compound → 6-Amino-1-benzyl-N-(3,4-difluorobenzyl)-2-isopropyl-1H-indole-3-carboxamide

HRID 40122Notes

Reaction equation

HRID 40122 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([N+:17]([O-])=O)[CH:15]=2)[C:10]([C:20]([NH:22][CH2:23][C:24]2[CH:29]=[CH:28][C:27]([F:30])=[C:26]([F:31])[CH:25]=2)=[O:21])=[C:9]1[CH:32]([CH3:34])[CH3:33])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>CCOC(C)=O.[Pd]>[NH2:17][C:14]1[CH:15]=[C:16]2[C:11]([C:10]([C:20]([NH:22][CH2:23][C:24]3[CH:29]=[CH:28][C:27]([F:30])=[C:26]([F:31])[CH:25]=3)=[O:21])=[C:9]([CH:32]([CH3:33])[CH3:34])[N:8]2[CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:12][CH:13]=1

Participants

5

Reactant 2

HCID 59762312HCID 59762312, compound2×HCID 178418361HCID 178418361, compound

Product 1

HCID 597624316-Amino-1-benzyl-N-(3,4-difluorobenzyl)-2-isopropyl-1H-indole-3-carboxamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

General Procedure S. A solution of 1-benzyl-N-(3,4-difluorobenzyl)-2-isopropyl-6-nitro-1H-indole-3-carboxamide (Compound 124, 300 mg, 0.65 mmol) in EtOAc (5 ml) was treated with 10% Pd—C (6.8 mg, 0.065 mmol) and hydrogen gas under atmospheric pressure at room temperature for 16 h. The mixture was filtered and concentrated in vacuo. The residue was purified by chromatography on silica gel (0→50% EtOAc-hexanes) to yield the title compound as a yellow oil.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by chromatography on silica gel (0→50% EtOAc-hexanes)

Sources & evidence

ORD record
ord-607a5640c5ee44b0884c7023a59fd7d9
Source dataset
uspto-grants-2013_09
Patent number
US08524917B2

Reaction notes

Loading…