2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl → 3,4-bis(Benzyloxy)-6-[(4-fluorophenyl)methyl]pyridazine

Temperature

65 °C

To a solution of 3,4-bis(benzyloxy)-6-chloropyridazine (Intermediate 1) (1 g, 3.06 mmol), dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (0.117 g, 0.245 mmol) and palladium (II) acetate (0.027 g, 0.122 mmol) in tetrahydrofuran (6.12 ml) under nitrogen was added (4-fluorobenzyl)zinc(II) bromide (9.18 ml, 4.59 mmol) and the resulting red/brown mixture was heated at 65° C. for 24 hours. The reaction mixture was cooled, diluted with ethyl acetate and washed with saturated aqueous sodium bicarbonate solution, saturated ammonium chloride solution and brine. The organics were dried (MgSO4), filtered and solvent removed in vacuo to give a brown oil. The oil was purified by silica chromatography (eluting with 0-100% ethyl acetate in petrol) to yield the title compound (663 mg, 1.61 mmol, 97% yield).

1. temperatureThe reaction mixture was cooled
2. washwashed with saturated aqueous sodium bicarbonate solution, saturated ammonium chloride solution and brine
3. dry with materialThe organics were dried (MgSO4)
4. filtrationfiltered
5. customsolvent removed in vacuo
6. customto give a brown oil
7. customThe oil was purified by silica chromatography (eluting with 0-100% ethyl acetate in petrol)

ORD record

ord-79d2a819b452424ea811f23102e76484

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09290456B2