3-Fluoro-1-propanol → HCID 53339379, compound

Participants

Reaction Steps

To a stirred solution of 3-fluoropropan-1-ol (5 mg, 0.05 mmol) in 0.3 mL o DCM at rt was added Dess-Martin reagent (42 mg, 0.1 mmol). The mixture was stirred for 1 h at rt and 0.3 mL of DCE was added. It was filtered through a cotton pad into a stirred mixture of 4-(7-methoxybenzo[4,5]imidazo[1,2-a]pyrimidin-2-yl)aniline (5 mg, 0.017 mmol, prepared following General Experiment Procedures Q and R) and NaBH(AcO)3 (42 mg, 0.2 mmol) in 0.3 mL of DCE. The reaction was vigorously stirred for 5 min and quenched by adding Na2CO3 (2 mL, saturated). The mixture was extracted with EtOAc (3×5 mL) and the combined organic phase was washed with water (2×10 mL) and dried over MgSO4 and concentrated under reduced pressure. The crude product was purified by reversed phase HPLC (TFA buffered water/MeCN) to afford the title compound as an orange solid (5 mg, 53%, TFA salt). MS (ESI) m/z [M+H]+351.

Provenance & Evidence