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

HRID 240867Notes

Reaction equation

HRID 240867 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:17]3[C:12](=[CH:13][C:14]([C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([N+:24]([O-])=O)[CH:19]=4)=[CH:15][CH:16]=3)[N:11]([C:27]3[N:32]=[CH:31][N:30]=[C:29]([NH:33][CH3:34])[CH:28]=3)[CH:10]=2)=[CH:5][CH:4]=1>[Ni].CO.CN(C=O)C>[NH2:24][C:20]1[CH:19]=[C:18]([C:14]2[CH:13]=[C:12]3[C:17]([C:9]([C:6]4[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=4)=[CH:10][N:11]3[C:27]3[N:32]=[CH:31][N:30]=[C:29]([NH:33][CH3:34])[CH:28]=3)=[CH:16][CH:15]=2)[CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 1

HCID 509919276-(3-(4-methoxyphenyl)-6-(3-nitrophenyl)-1H-indol-1-yl)-N-methylpyrimidin-4-amine

Product 1

HCID 509920026-(6-(3-aminophenyl)-3-(4-methoxyphenyl)-1H-indol-1-yl)-N-methylpyrimidin-4-amine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21901440N,N-dimethylformamide methanolSolvent

Procedure

Methanol/DMF (1:1, 20 mL) was added to 6-(3-(4-methoxyphenyl)-6-(3-nitrophenyl)-1H-indol-1-yl)-N-methylpyrimidin-4-amine (100 mg, 0.22 mmol) and Raney nickel (about 50 mg). The mixture was stirred at room temperature for 24 hours under hydrogen gas (1 atm). The reaction solution was filtered using a diatomite pad and then concentrated under reduced pressure. The target compound was obtained as brown solid.

Workup

  1. filtrationThe reaction solution was filtered
  2. concentrationconcentrated under reduced pressure
  3. customThe target compound was obtained as brown solid

Sources & evidence

ORD record
ord-add23ebe5dae4368ab44c4a549d5dd02
Source dataset
uspto-grants-2014_02
Patent number
US08648089B2

Reaction notes

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