Potassium Carbonate → 2,2,2-Trifluoro-1-[2-(3-phenyl-pyrazol-1-yl)-phenyl]-ethanol

HRID 1620844Notes

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].[C:14]1([C:20]2[CH:24]=[CH:23][NH:22][N:21]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=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>[F:1][C:2]([F:13])([F:12])[CH:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:22]1[CH:23]=[CH:24][C:20]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[N:21]1)[OH:4]

Participants

Conditions

Temperature: 130 °C

Procedure

2,2,2-Trifluoro-1-(2-iodo-phenyl)-ethanol (0.331 g, 1.1 mmol), 3-phenyl pyrazole (0.144 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 taken 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 a crude product, which was purified by ISCO column chromatography using 5-10% ethyl acetate in hexane as solvent to afford 2,2,2-trifluoro-1-[2-(3-phenyl-pyrazol-1-yl)-phenyl]-ethanol (75 mg).

Workup

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

Sources & evidence

ORD record: ord-ef1f5f9a1bff4d789e9d6329618b3ef0
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772482B2

Reaction notes

Loading…