Sodium Carbonate → (4-methyl-piperazin-1-yl)-(4-{5-[2-(6-methyl-pyridin-2-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-pyridin-3-yl}-phenyl)-methanone

Participants

Reaction Steps

To a solution of 4-(5-bromo-pyridin-3-yl)-2-(6-methyl-pyridin-2-yl)-7H-pyrrolo[2,3-d]pyrimidine (Example 16) (1 eq, 0.273 mmol, 100 mg) and 4-(4-methylpiperazine-1-carbonyl)phenyl-boronic acid pinacol ester (ABCR GmbH & Co. KG, Karlsruhe, Germany) (1.1 eq, 0.300 mmol, 101 mg) in DME/EtOH (1:1, 2 ml), aqueous Na2CO3 solution (2 M, 3 eq, 0.82 mmol, 0.41 ml) and Pd(PPh3)4 (0.05 eq, 0.014 mmol, 16 mg) are added. The resulting mixture is heated using microwave radiation at 140° C. for 20 min. The mixture is diluted with water, basified with aqueous NaOH (1 M), extracted with DCM, and the organic layer is dried with MgSO4 and filtered. After evaporation of the solvent the crude product is purified by reversed phase HPLC giving the title compound; [M+H]+=490; 1H-NMR (400 MHz, CDCl3): δ 13.09 (s, 1H), 9.50 (d, 1H), 8.98 (d, 1H), 8.78 (d, 1H), 8.66 (d, 1H), 7.84 (t, 1H), 7.76 (d, 2H), 7.58 (d, 2H), 7.45 (m, 1H), 7.33 (d, 1H), 6.87 (d, 1H), 3.84 (m, 2H), 3.53 (m, 2H), 2.74 (s, 3H), 2.55-2.35 (m, 4H), 2.34 (s, 3H).

Provenance & Evidence