Sodium Carbonate → 1-(2-(Benzyloxy)ethyl)-5-phenylpyridin-2(1H)-one

Participants

Reaction Conditions

Reaction Steps

A suspension of 1-(2-(benzyloxy)ethyl)-5-bromopyridin-2(1 H)-one (350 mg, 1.14 mmol), phenylboronic acid (277 mg, 2.27 mmol), 1,1′-bis(diphenylphosphino)ferrocene-palladium dichloride (83 mg, 114 μmol), Na2CO3 (1.70 mL, 3.41-mmol) [2M], and DME (3 mL) was sparged with argon for 10 min then heated to 85° C. for 60 min. The reaction mixture was partitioned between EtOAc and 5% NaHCO3. The organic residue was purified on 40 grams of silica eluting with 20-60% EtOAc/hexane to give a colorless oil. MS (ESI pos. ion) m/z (MH+): 306. Calc'd exact mass for C20H19NO2: 305. 1H NMR (400 MHz, Chloroform-d) δ ppm 3.77-3.89 (m, 2 H) 4.19-4.30 (m, 2 H) 4.50 (s, 2 H) 6.58-6.73 (m, 1 H) 7.17-7.45 (m, 10H) 7.59-7.71 (m, 2 H).

Provenance & Evidence