Sodium Carbonate → HCID 136069467, compound

Participants

Reaction Conditions

Reaction Steps

the intermediate 1a (8.7 g, 32.3 mmol) is placed in presence of tetrakis(triphenylphosphine)palladium(0) (1.12 g, 0.97 mmol) and sodium carbonate (6.85 g, 64.7 mmol) in a mixture of 50 mL of toluene and 50 mL of ethanol and the mixture is heated to 80° C. 1.2 equivalent of 4-hydroxyphenylboronic acid is added and the mixture is heated under reflux for 5 h and 1.2 additional equivalent of 4-hydroxyphenylboronic acid is added and the reflux is maintained throughout the night. Following concentration to dryness, the residue is taken up with water and is extracted using AcOEt. After drying the organic layers and concentration to dryness, the residue obtained is purified by flash chromatography (CH2Cl2-MeOH, gradient 100-0 to 97-3 over 40 min.). 0.7g of minority compound 1 is obtained and 8.2g of solid corresponding to the majority substituted mono product 4-chloro-5-(4-hydroxyphenyl)-2-(1-phenylethyl)-pyridazin-3(2H)-one is obtained (yield:78%).

Provenance & Evidence