[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([F:9])=[CH:4][N:3]=1.[O:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][C:18]=2B(O)O)[CH2:13][CH2:12][CH2:11]1.C(=O)([O-])[O-].[K+].[K+]>COCCOC.C(OCC)(=O)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[Cl:1][C:2]1[N:7]=[C:6]([C:18]2[CH:17]=[CH:16][CH:15]=[C:14]3[C:19]=2[O:10][CH2:11][CH2:12][CH2:13]3)[C:5]([F:9])=[CH:4][N:3]=1A batch with 2,4-dichloro-5-fluoropyrimidine (565 mg; 3.28 mmol; Aldrich Chemical Company Inc.), 3,4-dihydro-2H-chromen-8-ylboronic acid (643 mg; 3.61 mmol; Parkway Scientific LLC) and bis(triphenylphosphine)palladium(II)chloride (230 mg; 0.33 mmol) in 1,2-dimethoxyethane (5.4 mL) and 2 M solution of potassium carbonate (4.9 mL) was degassed using argon. The batch was stirred under argon for 16 hours at 90° C. After cooling the batch was diluted with ethyl acetate and washed with brine. The organic phase dried (sodium sulfate), filtered and concentrated. The residue was purified by chromatography (hexane/ethyl acetate 2%-20%) to give the desired product (701 mg; 2.57 mmol).
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