Water → HCID 53257340, compound

Participants

Reaction Steps

330 mg (6-Chloro-pyrimidin-4-yl)-[3-(2-morpholin-4-ylmethyl-benzoimidazol-1-ylmethyl)-phenyl]-amine (prepared in Example 92) (0.70 mmol) was suspended in 30 cm3 dimethoxyethane and the flask was filled with argon properly. 58 mg Tetrakis(thriphenylphosphine) palladium[0] (0.05 mmol) was added and the mixture was stirred at room temperature for 30 minutes. Then 152 mg 2-methoxyphenyl-boronic acid (1 mmol), 424 mg anhydrous Na2CO3 (4 mmol) and 6 ml water were added. The mixture was ferluxed overnight while slow argon flow was being applied. The reaction mixture was poured to 80 cm3 1M NaH2PO4 solution and it was extracted three times with 50-50 cm3 of ethyl-acetate. The combined organic layer was washed with brine, dried over MgSO4, decolorized with activated carbon and evaporated to dryness. The residual solid was recrystallized from minimal amount of acetonitrile and air-dried to give the desired product (132 mg, 37% yield). For analitical results and compound identification see Table 1.

Provenance & Evidence