Sodium Carbonate → N-{1-[6-(4-methoxyphenyl)pyridin-3-yl]-1-methylethyl}acetamide

Participants

Reaction Conditions

Reaction Steps

The product from Step B, 1-B, (37.11 g, 174 mmol), 4-methoxyphenylboronic acid (47.7 g, 314 mmol) and bis(triphenylphosphine)palladium(II) chloride (6.12 g, 8.72 mmol) were suspended in DMA (325 mL) and aq. 2.0 M Na2CO3 (288 mL, 576 mmol). The atmosphere of the reaction vessel was evacuated/purged with N2 (3×) and the reaction mixture was heated at 90° C. over 3 h. The reaction mixture was cooled to rt and partitioned between EtOAc and H2O. The organic layer was separated, washed with H2O, saturated aq. NaCl, dried (MgSO4), filtered and concentrated under reduced pressure. The residue was suspended in CH2Cl2 and the solid were isolated by vacuum filtration and dried under high vacuum. Alternative work-up: The reaction mixture was cooled to rt and diluted with H2O (1.85 L). The solids were collected by vacuum filtration rinsing with hexanes and dried under high vacuum. HPLC/MS: 285.0 (M+1); Rt=1.53 min.

Provenance & Evidence