N-methyl-2-pyrrolidone → HCID 86623628, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl (5-trifluoromethylsulfonyloxy-6-methylindan-1-yl)acetate (405 mg, 1.15 mmol, from Step E) in N-methylpyrrolidinone (5 mL), Pd2dba3 (5.00 mg, 0.00546 mmol), dppf (7 mg, 0.0127 mmol) and Zn(CN)2 were added under Ar. The reaction mixture was heated to 100° C. for 15 hr, cooled to ambient temperature and diluted with EtOAc. The organic layer was washed several times with H2O, dried (brine, MgSO4), filtered and concentrated in vacuo. Purification by flash chromatography (10% EtOAc/hexanes) on SiO2 afforded the 176 mg of the title compound as a white solid: 1H NMR (500 MHz, CDCl3) δ 1.71-1.90 (m, 1H), 2.36-2.60 (m, 5H), 2.71-2.82 (m, 1H), 2.82-2.96 (m, 2H), 3.55-3.68 (m, 1H), 3.76 (s, 3H), 7.11 (s, 1H), 7.47 (s, 1H).

Provenance & Evidence