Sodium Carbonate → HCID 178451795, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-(4-(4-chloro-5-(4-(trifluoromethyl)phenyl)-1H-imidazol-2-yl)-5,6-dihydropyridin-1(2H)-yl)-3-(trifluoromethyl)pyridine (60 mg, 0.127 mmol, Example 23(c)), 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (59 mg, 0.19 mmol, Chemshop), dichloro-bis(triphenyl-phosphine) palladium (II) (5 mg, 0.006 mmol, Aldrich), sodium carbonate (27 mg, 0.254 mmol), and DME/H2O/EtOH (7:3:2) solution (0.8 mL) was heated at 130° C. in a microwave synthesizer for 2 h. The reaction mixture was cooled to RT and filtered. The filter cake was washed with MeOH (2×1 mL) and the combined filtrates were concentrated in vacuo. The residue was dissolved in DMSO (1 mL) and purified by by preparative HPLC [gradient 10-85% MeCN (0.1% TFA)/H2O (0.1% TFA)]. The fractions containing the desired product were combined and treated with sat. aqueous solution of NaHCO3 (15 mL) at 0° C. for 24 h. The organic layer was separated, dried over MgSO4, and filtered. The filtrate was evaporated and the residue dried in vacuo to give the title compound as an orange solid. MS (ESI, positive ion) m/z: 620 (M+1).

Provenance & Evidence