Cyclopropylacetylene → HCID 86758856, compound

Participants

Reaction Steps

To a solution of N-[1-(4-cyano-3-fluoro-phenyl)-1-(3-methyl-3H-imidazol-4-yl)-ethyl]-2ethylpropanesulfinamide (Example 1, Step I) (0.50 g, 1.50 mmol) in THF (12 mL) at 0° C. in an ice-H2O bath was added cyclopropylethynyl magnesium bromide (3 mL of a 2M solution in Et2O prepared from cyclopropyl acetylene and ethyl magnesium bromide). Grignard reagent was added until the reaction mixture color remained dark brown/black. After 1 h the reaction mixture was quenched with H2O, diluted with CH2Cl2 and aqueous saturated NaHCO3 solution, layers separated, the aqueous layer washed with CH2Cl2 (2×), the organics combined, and dried (MgSO4). Filtration and concentration in vacuo gave the title compound as a 77/22 ratio of diastereomers.

Provenance & Evidence