Triethylamine → 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid [2-(2,4-dichloro-phenyl)-1-fluoromethyl-ethyl]-methoxy-amide

HRID 1039342Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][CH:10]([NH:13][O:14][CH3:15])[CH2:11][F:12].C(N(CC)CC)C.[F:23][CH:24]([F:34])[C:25]1[C:29]([C:30](Cl)=[O:31])=[CH:28][N:27]([CH3:33])[N:26]=1>ClCCl.O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][CH:10]([N:13]([O:14][CH3:15])[C:30]([C:29]1[C:25]([CH:24]([F:34])[F:23])=[N:26][N:27]([CH3:33])[CH:28]=1)=[O:31])[CH2:11][F:12]

Participants

Conditions

Temperature: 24 °C

Procedure

To a stirred solution of N-[2-(2,4-dichlorophenyl)-1-fluoromethyl-ethyl]-O-methyl-hydroxylamine (0.21 g; 0.82 mmol), prepared as described in example P7c and triethylamine (0.13 ml; 0.90 mmol) in dichloromethane (1.9 ml) under nitrogen at 15° C. was added dropwise 3-difluoromethyl-1-methyl-1H-pyrazole-4-carbonyl chloride (0.16 g; 0.82 mmol). The reaction mixture was stirred at 24° C. for 16 h under nitrogen. The mixture was poured in water and extracted three times with dichloromethane. Combined organics were dried over sodium sulfate and the solvent was removed in vacuo. The crude was subject to flash chromatography (eluant: c-hexane/ethyl acetate 90:10 to 10:90) to afford 0.22 g (64% of theory) of 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid [2-(2,4-dichloro-phenyl)-1-fluoromethyl-ethyl]-methoxy-amide as a yellow oil.

Workup

extractionextracted three times with dichloromethane
dry with materialCombined organics were dried over sodium sulfate
customthe solvent was removed in vacuo

Sources & evidence

ORD record: ord-eec115486e7048c7b74dae7346ce3627
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08552049B2

Reaction notes

Loading…