4-Methylpyrazole → 2,2,2-Trifluoro-1-[5-methoxy-2-(4-methyl-pyrazol-1-yl)-phenyl]-ethanol

Participants

Role	Name	HCID	Charge
Reactant	4-Methylpyrazole	HCID 3406	—
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	trans-N,N'-dimethyl-1,2-cyclohexanediamine	HCID 2733821	—
Reactant	1-(2-Bromo-5-methoxyphenyl)-2,2,2-trifluoroethan-1-ol	HCID 66742671	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	Toluene	HCID 1140	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	2,2,2-Trifluoro-1-[5-methoxy-2-(4-methyl-pyrazol-1-yl)-phenyl]-ethanol	HCID 66743424	15.7%

Reaction Conditions

Temperature	130 °C

Reaction Steps

1-(2-Bromo-5-methoxy-phenyl)-2,2,2-trifluoro-ethanol (0.570 g, 2.0 mmol), 4-methyl pyrazole (0.164 g, 2.0 mmol), CuI (0.057 g, 0.3 mmol), K2CO3 (0.580g, 4.2 mmol), (1R,2R)-N,N′-dimethyl-cyclohexane-1,2-diamine (0.071 g, 0.5 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 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-[5-methoxy-2-(4-methyl-pyrazol-1-yl)-phenyl]-ethanol (90 mg).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07968559B2
Source dataset	uspto-grants-2011_06
ORD ID	ord-ff5deb28cc2b493088ccefd2feb077e0
Source note	uspto-grants-2011_06