4-(4-fluoro-2-methoxyphenyl)-N-(3-nitrophenyl)pyridin-2-amine → N-(4-(4-fluoro-2-methoxyphenyl)pyridin-2-yl)benzene-1,3-diamine

HRID 593290Notes

Reaction equation

HRID 593290 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([NH:14][C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-])=O)[CH:16]=3)[CH:9]=2)=[C:4]([O:24][CH3:25])[CH:3]=1>C1COCC1.CO.[Pd]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([NH:14][C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([NH2:21])[CH:16]=3)[CH:9]=2)=[C:4]([O:24][CH3:25])[CH:3]=1

Participants

4

Reactant 1

HCID 601965424-(4-fluoro-2-methoxyphenyl)-N-(3-nitrophenyl)pyridin-2-amine

Product 1

HCID 60197054N-(4-(4-fluoro-2-methoxyphenyl)pyridin-2-yl)benzene-1,3-diamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of C2 (98 mg, 0.29 mmol) in THF/MeOH 1:1 (20 mL) was added Pd/C (10% w/w, 46 mg). The reaction mixture was stirred under hydrogen atmosphere (1 atm) at RT for 15 hours. The suspension was filtered through a pad of Celite® and the solvent was removed in vacuo to leave the desired product I1 as a brown solid (89 mg, 99%). MS (ES) C18H16FN3O requires: 309. found: 310 (M+H)+.

Workup

  1. filtrationThe suspension was filtered through a pad of Celite®
  2. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-cd3ccc033fa348abbed4e3a27b96372a
Source dataset
uspto-grants-2016_01
Patent number
US09242937B2

Reaction notes

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