Sodium Carbonate → HCID 68977110, compound

Participants

Reaction Steps

2-(4-Bromo-phenyl)-5-methyl-2,4-dihydro-pyrazol-3-one (105 mg) was dissolved in DME (ethylene glycol dimethyl ether, 2 mL), then Pd(PPh3)4 (15 mg, 3% mol) was added. The air was exchanged with argon and the mixture was stirred for 10 min. A solution of 2-(3-methoxy-4-methoxymethoxy-phenyl)-vinyl-boronic acid (90 mg) in DME (1 mL) was added followed by sodium carbonate solution (2M, 0.75 mL). The mixture was stirred for 1 hour at 110° C. After partitioning with ethyl acetate and water and purification over silica gel eluting with 50% EtOAc in hexane gave 140 mg of 2-{4-[2-(3-methoxy-4-methoxymethoxy-phenyl)-vinyl]-phenyl}-5-methyl-2,4-dihydro-pyrazol-3-one as an oily product, which was then hydrolyzed with conc. HCl in methanol. Evaporation of the solvent and purification over silica gel gave 2-{4-[2-(4-hydroxy-3-methoxy-phenyl)-vinyl]-phenyl}-5-methyl-2,4-dihydro -pyrazol-3-one as a light yellow solid (90 mg). 1HNMR (CDCl3, 300 MHz): 7.74 (d, J=8.6 Hz, 2H), 7.30 (d, J=8.6 Hz, 2H), 6.77 (s, 3H), 6.48 (s 2H), 5.66 (s, 1H), 3.63 (s, 3H), 3.42 (s, 2H), 2.19(s, 3H) ppm. 13CNMR (CDCl3—CD3OD, 75 MHz): 170.48, 156.45, 146.04, 144.89, 136.70, 134.28, 129.97, 129.41, 128.00, 122.47, 118.46, 114.21, 111.14, 55.72, 43.10, 17.05 ppm. MS (m/z): 323 (MH+).

Provenance & Evidence