Cesium fluoride → HCID 66678410, compound

Participants

Reaction Steps

A mixture of methyl 4-bromo-3-hydroxybenzoate (Combi-Blocks CA-4189, 3.00 g, 13.0 mmol), 2-ethylphenylboronic acid (2.92 g, 19.5 mmol), cesium fluoride (5.92 g, 39.0 mmol; 3.00), palladium acetate (58 mg, 0.26 mmol) and 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (320 mg, 0.78 mmol) was prepared in dioxane (30 mL) and water (15 mL) and heated at 90° C. for 2 hours. Additional amounts of 2-ethylphenylboronic acid (1.46 g, 9.7 mmol), palladium acetate (58 mg, 0.26 mmol) and 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (320 mg, 0.78 mmol) were added, and the mixture was stirred for 2 additional hours. Additional amounts of 2-ethylphenylboronic acid (0.73 g, 4.9 mmol), palladium acetate (29 mg, 0.13 mmol) and 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (160 mg, 0.39 mmol) were added, and the mixture was stirred for 2 additional hours. The reaction mixture was diluted with MTBE (150 mL), and then washed with water (50 mL) and brine (50 mL). The aqueous layers were extracted with MTBE (75 mL). The organic layers were combined, dried (MgSO4) and concentrated under vacuum. After purification by flash chromatography (silica, heptane/EtOAc), the title compound was obtained as a yellow oil (3.13 g, 94%). HPLC (Method A) Rt 4.5 min (Purity: 99.2%). LC/MS (Method B): 255.1 (M−H)−.

Provenance & Evidence