Triethylamine → 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (3-iodo-6,7,8,9-tetrahydro-5-H-benzocyclohepten-5-yl)-methoxy-amide

HRID 241508Notes

Reaction equation

[I:1][C:2]1[CH:15]=[CH:14][C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][CH:10]([NH:11][O:12][CH3:13])[C:4]=2[CH:3]=1.C(N(CC)CC)C.[CH3:23][N:24]1[CH:28]=[C:27]([C:29](Cl)=[O:30])[C:26]([C:32](F)([F:34])[F:33])=[N:25]1>ClCCl>[I:1][C:2]1[CH:15]=[CH:14][C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][CH:10]([N:11]([O:12][CH3:13])[C:29]([C:27]3[C:26]([CH:32]([F:34])[F:33])=[N:25][N:24]([CH3:23])[CH:28]=3)=[O:30])[C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 24 °C

Procedure

To a stirred solution of N-(3-iodo-6,7,8,9-tetrahydro-5-H-benzocyclohepten-5-yl)-O-methyl-hydroxylamine (77 mg; 0.24 mmol), prepared as described in example P3c and triethylamine (0.037 ml; 0.26 mmol) in dichloromethane (1.6 ml) under nitrogen at 4° C. was added dropwise 1-methyl-3-trifluoromethyl-1H-pyrazole-4-carbonyl chloride (47 mg; 0.24 mmol). The reaction mixture was stirred at 24° C. for 3 h under nitrogen. The mixture diluted with dichloromethane (10 ml), washed with 1M sodium hydroxide (1 ml), 1M hydrochloric acid (1 ml) and brine (1 ml). Organics were dried over sodium sulfate. The solvent was removed in vacuo. The crude (190 mg) was subject to flash chromatography (eluant: c-hexane/ethyl acetate 90:10 to 50:50) to afford 0.101 g (88% of theory) of 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (3-iodo-6,7,8,9-tetrahydro-5-H-benzocyclohepten-5-yl)-methoxy-amide as a yellow solid oil.

Workup

washwashed with 1M sodium hydroxide (1 ml), 1M hydrochloric acid (1 ml) and brine (1 ml)
dry with materialOrganics were dried over sodium sulfate
customThe solvent was removed in vacuo

Sources & evidence

ORD record: ord-9aa86ff200914857a5a46f90941edd68
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653003B2

Reaction notes

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