Dibutyltin dichloride → HCID 66619416, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 7 mg (0.023 mmol) dibutyltin dichloride in 1 ml tetrahydrofuran were added 0.10 g (0.23 mmol) [2-(4-chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-cyclohexyl-acetaldehyde (Example 143, intermediate c), 0.038 g (0.23 mMol) 4-aminobenzonitrile (commercially available) and 0.06 ml (0.46 mmol) phenylsilane (commercially available). The pale yellow solution was heated to 100° C. under microwave irradiation for 21 min. The light yellow solution was treated with silica gel and the suspension evaporated to dryness. The remaining solid was purified by silica gel chromatography using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of heptane:ethyl acetate (100:0 to 70:30). The fractions containing the product were pooled and chromatographed a second time under the same conditions to give the title compound as a white solid (67%). MS (Turbo Spray): m/z=491.2 [M+H].

Provenance & Evidence