HCID 67155027, compound → HCID 69937586, compound

Participants

Reaction Conditions

Reaction Steps

To 2-(4-acetyl-5-fluoropyridin-3-yl)benzofuran-5-carbonitrile 11b (200 mg, 0.714 mmol) in THF (3.57 mL) at −78° C. was added methylmagnesium bromide (3M in Et2O, 0.714 mL, 2.142 mmol). The mixture was stirred for 1 hr at −78° C., and then for 1 hr at 0° C. The mixture was quenched with saturated NH4Cl and extracted with EtOAc two times, dried over magnesium sulfate, filtered and concentrated. The residue was purified via Biotage (10-40% EtOAc/heptane; SNAP25 column), and then purified on Waters mass directed preparative-HPLC (ACN—H2O—NR4OH, Xbridge Preparation C18 column, 30×100 mm) giving the title compound 11 (60 mg, 28%). 1H NMR (400 MHz, MeOD) δ ppm 1.70 (d, J=1.96 Hz, 6H) 6.94 (s, 1H) 7.55-7.71 (m, 2H) 8.00-8.11 (m, 1H) 8.39 (s, 1H) 8.53 (d, J=3.73 Hz, 1H). LC-MS (M+1) 297.1, t=1.50 min.

Provenance & Evidence