6-(6-(4-methoxyphenyl)-3-(3-nitrophenyl)-1H-indol-1-yl)-N-methylpyrimidin-4-amine → 6-(3-(3-aminophenyl)-6-(4-methoxyphenyl)-1H-indol-1-yl)-N-methylpyrimidin-4-amine

HRID 240859Notes

Reaction equation

HRID 240859 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:17]=[C:16]3[C:12]([C:13]([C:26]4[CH:31]=[CH:30][CH:29]=[C:28]([N+:32]([O-])=O)[CH:27]=4)=[CH:14][N:15]3[C:18]3[N:23]=[CH:22][N:21]=[C:20]([NH:24][CH3:25])[CH:19]=3)=[CH:11][CH:10]=2)=[CH:5][CH:4]=1>[Ni].CO.CN(C=O)C>[NH2:32][C:28]1[CH:27]=[C:26]([C:13]2[C:12]3[C:16](=[CH:17][C:9]([C:6]4[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=4)=[CH:10][CH:11]=3)[N:15]([C:18]3[N:23]=[CH:22][N:21]=[C:20]([NH:24][CH3:25])[CH:19]=3)[CH:14]=2)[CH:31]=[CH:30][CH:29]=1

Participants

4

Reactant 1

HCID 509918416-(6-(4-methoxyphenyl)-3-(3-nitrophenyl)-1H-indol-1-yl)-N-methylpyrimidin-4-amine

Product 1

HCID 509918426-(3-(3-aminophenyl)-6-(4-methoxyphenyl)-1H-indol-1-yl)-N-methylpyrimidin-4-amineYield 89%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21901440N,N-dimethylformamide methanolSolvent

Procedure

Methanol/DMF (2:1, 20 mL) was added to 6-(6-(4-methoxyphenyl)-3-(3-nitrophenyl)-1H-indol-1-yl)-N-methylpyrimidin-4-amine (70 mg, 0.16 mmol) and Raney nickel (Raney Ni; about 50 mg). The mixture was stirred at room temperature for 12 hours under hydrogen gas (1 atm). The reaction solution was filtered using a diatomite pad and concentrated under reduced pressure. The target compound (60 mg) was obtained as brown solid.

Workup

  1. filtrationThe reaction solution was filtered
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-58d9ed270a0a49b59121c58b65ffd0a1
Source dataset
uspto-grants-2014_02
Patent number
US08648089B2

Reaction notes

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