4-Methyl-2-(3-fluoro-phenyl)-pyrimidine-5-carboxylic acid (5-nitro-indol-1-yl)-amide → 2-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (5-amino-indol-1-yl)-amide

HRID 2382110Notes

Reaction equation

HRID 2382110 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([NH:13][C:14]([C:16]1[C:17]([CH3:29])=[N:18][C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[CH:23]=3)=[N:20][CH:21]=1)=[O:15])[CH:8]=[CH:7]2)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([NH:13][C:14]([C:16]1[C:17]([CH3:29])=[N:18][C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[CH:23]=3)=[N:20][CH:21]=1)=[O:15])[CH:8]=[CH:7]2

Participants

4

Reactant 1

HCID 591999564-Methyl-2-(3-fluoro-phenyl)-pyrimidine-5-carboxylic acid (5-nitro-indol-1-yl)-amide

Product 1

HCID 591999982-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (5-amino-indol-1-yl)-amideYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 4-methyl-2-(3-fluoro-phenyl)-pyrimidine-5-carboxylic acid (5-nitro-indol-1-yl)-amide (1.64 mmol) in MeOH (45 mL) and 10% Pd/C (0.16 mmol) is hydrogenated in a 500 mL Parr bottle under 50 psi at rt overnight. Pd/C is filtered off. The filtrate is concentrated to afford 2-(3-fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (5-amino-indol-1-yl)-amide (545 mg, 92%) as a solid. MS: 362 (M+H); 1H NMR (300 MHz, CD3OD): δ 3.84(s, H), 6.37(d, H), 6.81(dd, H), 7.01(d, H), 7.16-7.36(m, 3H), 7.55(m, H), 8.23(d, H), 8.36(d, H), 9.50(s, H).

Workup

  1. filtrationPd/C is filtered off
  2. concentrationThe filtrate is concentrated

Sources & evidence

ORD record
ord-d51087ae1fff477ba3c64f003a847c8e
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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