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 2192275Notes

Reaction equation

HRID 2192275 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-1f4e6e418d5f432f9a702c31310746c2
Source dataset
uspto-grants-2012_12
Patent number
US08329708B2

Reaction notes

Loading…