1,2-Dimethoxyethane → HCID 59475104, compound

Participants

Reaction Steps

In a sulfonation flask a mixture containing of 207 mg (0.5 mmol) 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid[2-(5-bromo-3-chlorothiophen-2-yl)-1-methylethyl]amide, 90 mg (0.64 mmol) 4-fluorophenylboronic acid, 151 mg (1.8 mmol) sodiumbicarbonate, 36 mg (0.05 mmol) bistriphenylphosphine palladium dichloride, 10 ml dimethoxyethane and 5 ml of water is stirred at reflux for 6 hours. After cooling to ambient temperature ethylacetate and water is added and the organic layer separated and washed again twice with water. After drying (sodium sulphate) and distilling off the solvent in a water jet vacuum, the crude product is obtained. Purification is achieved by column chroma-tography over silicagel (eluent: ethylacetate/heptane 1:1). Yield: 180 mg (80% of theory) of a slightly brown oil (1H-NMR: 1.29/d/3H, 0.9/m/2H, 3.09/m/2H, 3.89/s/3H, 4.42/m/1H, 6.38/s (broad)/1H, 6.89/t/1H—CF2H, 7.05/m/2H, 7.48/m/2H, 7.89/s/1H).

Provenance & Evidence