HCID 67112859, compound → HCID 67113010, compound

HRID 2284315Notes

Reaction equation

HRID 2284315 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([NH:13][C:14]3[CH:22]=[C:21]4[C:17]([C:18]([C:23]5[CH:28]=[CH:27][C:26]([N+:29]([O-])=O)=[CH:25][CH:24]=5)=[CH:19][NH:20]4)=[CH:16][CH:15]=3)=[O:12])=[CH:8][CH:9]=2)[CH:4]=[CH:3]1.[H][H]>C(O)C.[OH-].[OH-].[Pd+2]>[NH2:29][C:26]1[CH:25]=[CH:24][C:23]([C:18]2[C:17]3[C:21](=[CH:22][C:14]([NH:13][C:11]([C:7]4[CH:6]=[C:5]5[C:10](=[CH:9][CH:8]=4)[N:2]([CH3:1])[CH:3]=[CH:4]5)=[O:12])=[CH:15][CH:16]=3)[NH:20][CH:19]=2)=[CH:28][CH:27]=1

Participants

5

Reactant 2

HCID 67112859HCID 67112859, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67113010HCID 67113010, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

To a slurry of 1-methyl-N-(3-(4-nitrophenyl)-1H-indol-6-yl)-1H-indole-5-carboxamide (59.0 mg, 0.14 mmol) in ethanol (1.50 mL) under an atmosphere of nitrogen was added 20 wt % palladium hydroxide on carbon (5.9 mg, 10 wt %), followed by a balloon of hydrogen. The reaction was stirred overnight at room temperature and was then filtered through a pad of Celite, rinsing with excess methanol and methylene chloride. The filtrate was concentrated to give a grey-pink solid for N-(3-(4-aminophenyl)-1H-indol-6-yl)-1-methyl-1H-indole-5-carboxamide (56.9 mg, 0.14 mmol, 100%).

Workup

  1. filtrationwas then filtered through a pad of Celite
  2. washrinsing with excess methanol and methylene chloride
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-c36ccf0aa5d54ba8a7bd7d3f3a361ac4
Source dataset
uspto-grants-2015_09
Patent number
US09144557B2

Reaction notes

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