Toluene → HCID 86614073, compound

Participants

Reaction Conditions

Reaction Steps

A 100 mL round-bottomed flask was charged with 3-(4-(piperidin-1-yl)styryl)-2-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (199 mg, 0.49 mmol), 4-chloro-N-methylpyrimidin-2-amine (146 mg, 1.016 mmol) and Pd(PPh3)4 (59 mg, 50.9 μmol). Then toluene (20 mL), EtOH (10 mL) and 2M aq. K2CO3 (1.53 mL, 3.05 mmol) were added and the reaction mixture was immersed in an oil bath at 120° C. for 1 h. The reaction mixture was partitioned between EtOAc (30 mL) and water (50 mL) and the organic layer was dried (MgSO4), filtered and concentrated and then quickly filtered through silica (MeOH/CH2Cl2 gradient). After evaporation of volatiles the residue was dissolved in dioxane (8 mL) and water (3 mL) and concentrated HCl (0.66 mL) was added. The reaction mixture was heated to 110° C. for 70 min and then evaporated. Purification by reverse phase preparative HPLC (eluting with aq. TFA/MeCN) gave the title compound (40 mg, 21%) as a yellow solid.

Provenance & Evidence