Methyl iodide → HCID 58088354, compound

Participants

Reaction Conditions

Reaction Steps

A solution of diisopropylamine (120 μL, 0.849 mmol) and THF (4 mL) is cooled to −78° C. A solution of n-butyl lithium (1.6 M in hexanes, 487 μL, 0.779 mmol) is added dropwise and the reaction is stirred for 40 minutes at −78° C. A solution of 6-{4-[5-cyclopropyl-3-(2-trifluoromethoxy-phenyl)-isoxazol-4-ylmethoxy]-2-methyl-phenyl}-benzo[b]thiophene-3-carboxylic acid (200 mg, 0.354 mmol) in THF (2 mL) is added dropwise and the resulting yellow solution is stirred at −78° C. for one hour. Methyl iodide (221 μL, 3.54 mmol) is added dropwise and the reaction is allowed to gradually warm to ambient temperature overnight. The flask is cooled in an ice bath and saturated aqueous ammonium chloride (5 mL) is added. The mixture is diluted with water and ethyl acetate. The ethyl acetate layer is washed with brine, dried over MgSO4, and concentrated under reduced pressure. The residue is purified via radial chromatography eluting with 2% MeOH—CH2Cl2. The purification is repeated for impure fractions containing product. The title compound (44 mg, 21%) is obtained as a gray solid.

Provenance & Evidence