3,5-Dimethylpyrazole → 1-[2-(3,5-Dimethyl-pyrazol-1-yl)-phenyl]-2,2,2-trifluoro-ethanol

HRID 2426407Notes

Reaction equation

[F:1][C:2]([F:13])([F:12])[CH:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1I)[OH:4].[CH3:14][C:15]1[CH:19]=[C:18]([CH3:20])[NH:17][N:16]=1.C([O-])([O-])=O.[K+].[K+].CN[C@@H]1CCCC[C@H]1NC>C(OCC)(=O)C.[Cu]I.C1(C)C=CC=CC=1>[CH3:14][C:15]1[CH:19]=[C:18]([CH3:20])[N:17]([C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[CH:3]([OH:4])[C:2]([F:13])([F:12])[F:1])[N:16]=1

Participants

Conditions

Temperature: 130 °C

Procedure

2,2,2-Trifluoro-1-(2-iodo-phenyl)-ethanol (0.331 g, 1.1 mmol), 3,5-dimethyl pyrazole (0.096 g, 1.0 mmol), CuI (0.019 g, 0.1 mmol), K2CO3 (0.290 g, 2.1 mmol), (1R,2R)-N,N′-dimethyl-cyclohexane-1,2-diamine (0.028 g, 0.2 mmol) and toluene (10 ml) were combined in a 20 ml pressure tube and the mixture was heated at 130° C. (oil bath temperature) for 12 h. The mixture was diluted with ethyl acetate and washed with H2O (2×20 ml), brine, and dried over sodium sulfate. Removal of solvent gave crude product, which was purified by ISCO column chromatography using 5-10% ethyl acetate in hexane as solvent to give 1-[2-(3,5-dimethyl-pyrazol-1-yl)-phenyl]-2,2,2-trifluoro-ethanol (120 mg).

Workup

washwashed with H2O (2×20 ml), brine
dry with materialdried over sodium sulfate
customRemoval of solvent
customgave crude product, which
customwas purified by ISCO column chromatography

Sources & evidence

ORD record: ord-aafc0fc3e4e04af1b6ec7dc966744a1e
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07968559B2

Reaction notes

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