(5-fluoro-2-nitrophenyl)-(1-methyl-1H-pyrazol-4-yl)amine → 4-Fluoro-N2-(1-methyl-1H-pyrazol-4-yl)-benzene-1,2-diamine

HRID 243190Notes

Reaction equation

[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:15]([O-])=O)=[C:6]([NH:8][C:9]2[CH:10]=[N:11][N:12]([CH3:14])[CH:13]=2)[CH:7]=1>[Pd].CCOC(C)=O>[F:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:10]=[N:11][N:12]([CH3:14])[CH:13]=2)[C:5]([NH2:15])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 20 °C

Procedure

A mixture of (5-fluoro-2-nitrophenyl)-(1-methyl-1H-pyrazol-4-yl)amine (102 mg, 0.43 mmol) and 10% palladium on carbon (25 mg) in EtOAc (10 mL) was stirred under an atmosphere of hydrogen at atmospheric pressure and 20° C. for 6 h. A separate mixture of (5-fluoro-2-nitrophenyl)-(1-methyl-1H-pyrazol-4-yl)amine (0.19 g, 0.80 mmol) and 10% palladium on carbon (50 mg) in EtOAc (10 mL) was stirred under an atmosphere of hydrogen at atmospheric pressure and 20° C. for 5 h. The catalyst was removed by filtration and the filtrates combined and concentrated in vacuo. The resulting residue was purified by chromatography (SiO2, 0-8% (2M ammonia in methanol) in DCM) to give the title compound as a brown oil (0.188 g, 74%). LCMS (Method C): RT 1.61 min [M+H]+ 207.1

Workup

stirringwas stirred under an atmosphere of hydrogen at atmospheric pressure and 20° C. for 5 h
customThe catalyst was removed by filtration
concentrationconcentrated in vacuo
customThe resulting residue was purified by chromatography (SiO2, 0-8% (2M ammonia in methanol) in DCM)

Sources & evidence

ORD record: ord-d50d681132a24c71886a085295997328
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653089B2

Reaction notes

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