Methyl iodide → 4-Amino-2-(2-fluorophenyl)-1,5-dimethyl-1H-pyrazol-3(2H)-one

HRID 1478824Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12](=[O:13])[CH:11]=[C:10]([CH3:14])[N:9]1[CH3:15].FC1C=CC=CC=1[N:23]1C(=O)C=C(C)N1.IC.C([O-])([O-])=O.[K+].[K+]>C1COCC1>[NH2:23][C:11]1[C:12](=[O:13])[N:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[F:1])[N:9]([CH3:15])[C:10]=1[CH3:14]

Participants

Conditions

Temperature: 65 °C

Procedure

2-(2-Fluorophenyl)-1,5-dimethyl-1H-pyrazol-3(2H)-one To a solution of 2-(2-fluorophenyl)-5-methyl-1H-pyrazol-3(2H)-one (500 g, 2602 mmol) in THF (2500 ml) heated to 58° C. was added iodomethane (163 ml) dropwise over 15 mins and the mixture was stirred at 65° C. for 30 mins. K2CO3 (198 g) was added over 20 mins and stirred for 16 hrs. Further iodomethane (16.3 ml) was added and stirring continued for 1 hr. The resulting mixture was cooled to 0° C., filtered and washed with THF (50 ml). The filtrate was evaporated to dryness and purified by column chromatography, eluting with EtOAc/Heptane to give the title compound as a red solid.

Workup

stirringstirred for 16 hrs
stirringstirring
waitcontinued for 1 hr
temperatureThe resulting mixture was cooled to 0° C.
filtrationfiltered
washwashed with THF (50 ml)
customThe filtrate was evaporated to dryness
custompurified by column chromatography
washeluting with EtOAc/Heptane

Sources & evidence

ORD record: ord-b001874160e04ab09e881f8b5dec3c80
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09403833B2

Reaction notes

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