Sodium hydride → 1-(2-(Benzyloxy)ethyl)-5-bromopyridin-2(1H)-one

Participants

Reaction Conditions

Reaction Steps

To a stirring solution of 5-bromo-2(1 h)-pyridone (2000 mg, 11.5 mmol) in DMF (15 mL) at 0° C. was added NaH (60% dispersion in mineral oil, 552 mg, 23.0 mmol). After 1 h then 1-((2-bromoethoxy)methyl)benzene (2.00 mL, 12.6 mmol) was added. The reaction mixture was heated to 50° C. for 18 h. NH4Cl (satd.) was added and the mixture was partitioned between EtOAc and water. The aqueous layer was extracted twice with EtOAc (50 mL) and the combined organic was washed with satd. NH4Cl and dried over MgSO4. The organic was concentrated to an oil by repeatedly azeotroping with toluene. This residue was purified on 40 grams of silica eluting with 15-30% of EtOAc/hexanes to give a colorless oil that crystallized upon sitting for 2 weeks. MS (ESI pos. ion) m/z (MH+): 308/310. Calc'd exact mass for C14H14BrNO2: 307. 1H NMR (400 MHz, Chloroform-d) δ ppm 3.71-3.76 (m, 2 H) 4.08-4.13 (m, 2 H) 4.48 (s, 2 H) 6.46 (d, J=9.78 Hz, 1H) 7.21-7.38 (m, 6 H) 7.54 (d, J=2.74 Hz, 1 H).

Provenance & Evidence