Trifluoroacetic acid → HCID 178456061, compound

Participants

Reaction Conditions

Reaction Steps

Argon was bubbled through a mixture of (S)-tert-butyl (1-(5-bromo-1H-benzo[d]imidazol-2-yl)propyl)carbamate (Preparation 18, 150 mg, 0.42 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (48.2 mg, 0.0659 mmol), and neopentylzinc bromide in tetrahydrofuran (0.5 M, 2.5 mL, 1.3 mmol) for 5 minutes. The mixture was then heated under microwave irradiation for 10 minutes at 140° C. After cooling, the reaction was concentrated in vacuo, redissolved in dichloromethane (9 mL) and treated with trifluoroacetic acid (1 mL, 13 mmol). After stirring for 2.5 hours, the reaction was concentrated in vacuo and redissolved in a saturated solution of hydrogen chloride in methanol and stirred for 18 hours. The fully deprotected product was concentrated in vacuo and purified by preparative HPLC followed by silica gel column chromatography eluting with 0-50% CMA80/methylene chloride to afford the title compound (10 mg, 15%) as a white solid.

Provenance & Evidence