Reaction #108

ord-373fd601db1247b0b18c34bca387c3a4

Reaction equation

CN1Cc2ccc(Cl)nc2OC(c2cccnc2)C1
CN1Cc2ccc(Cl)nc2OC(c
COc1cc(N)ccc1-n1cnc(C)c1
COc1cc(N)ccc1-n1cnc(
COc1cc(Nc2ccc3c(n2)OC(c2cccnc2)CN(C)C3)ccc1-n1cnc(C)c1
COc1cc(Nc2ccc3c(n2)O
Yield 27.8%

Solvents

Conditions

Temperature
100°CELSIUS

Procedure

[Reactants], Palladium(II) acetate (5.29 mg, 0.02 mmol), 2-(Dicyclohexylphosphino)biphenyl (8.26 mg, 0.02 mmol) and Cesium carbonate (0.230 g, 0.71 mmol) were placed in a microwave vial and flushed with argon. DME (2 mL) was added and the reaction mixture was run in the microwave at 100°C for 60 minutes. Reaction not complete. Added 0.1 eq of Palladium(II) acetate (5.29 mg, 0.02 mmol) and 0.1 eq of 2-(Dicyclohexylphosphino)biphenyl (8.26 mg, 0.02 mmol) and flushed with argon. Run in the microwave at 100°C for 60 minutes and the reaction was complete. The reaction mixture was filtrated through celite and concentrated. The crude product was purified by prep-HPLC. The solvent was evaporated and partitioned between sat. NaHCO3 and dichloromethane. The organic layer was separated, dried (MgSO4) and concentrated giving 0.029 g (28%) of the product.

Source

750 AstraZeneca ELN dataset