Sodium Carbonate → HCID 89580074, compound

Participants

Reaction Conditions

Reaction Steps

As shown in Scheme 4, a suspension of 2-chloro-6-vinylpyrimidine-4-carboxylic acid (9) (4.38 g, 0.02 mol), 2-(4-(4-fluorophenoxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (22) (7.45 g, 0.02 mol), Na2CO3 (5.3 g, 0.05 mol), and PdCl2(PPh3)2 (Aldrich, 701 mg, 1.0 mmol) in dimethoxy ethane(DME)/EtOH/H2O (500 mL, 2:1:2 ratio) was degassed by repeating with Ar2/vacuum cycles. The mixture was heated at 90° C. for 23 h. Upon cooling to the room temperature, the mixture was poured into DCM. The solids were filtered off and the filtrates were washed with H2O and the aqueous phase was extracted with EtOAc. The combined organic layers were dried with anhydrous MgSO4 and concentrated to give 2-(4-(4-fluorophenoxy)phenyl)-6-vinylpyrimidine-4-carboxylic acid (23) pale yellow oil which was then purified by column chromatography (EtOAc:Hexanes=1:1) to give 6.5 g (82% yield), Rf=0.3 (DCM:MeOH=9:1); LC/MS: m/z=337 [M+H]+.

Provenance & Evidence