Reaktion #257

ord-e759d69f11ae4651a16a93e70cd9c7e3

Reaktionsgleichung

Fc1cccn2c(-c3nc(Cl)ncc3Cl)cnc12
Fc1cccn2c(-c3nc(Cl)n
COc1cc(N(C)CC(=O)OC(C)(C)C)ccc1N
COc1cc(N(C)CC(=O)OC(
COc1cc(N(C)CC(=O)OC(C)(C)C)ccc1Nc1ncc(Cl)c(-c2cnc3c(F)cccn23)n1
COc1cc(N(C)CC(=O)OC(
Ausbeute 43.0%

Lösungsmittel

Reaktionsbedingungen

Temperatur
100°CELSIUS

Vorschrift

A microwave tube was charged with diacetoxypalladium (11.18 mg, 0.05 mmol), potassium phosphate (529 mg, 2.49 mmol),2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (62.0 mg, 0.10 mmol), 3-(2,5-dichloropyrimidin-4-yl)-8-fluoroimidazo[1,2-a]pyridine (282 mg, 1.00 mmol) purged with nitrogen. Dioxane (4.5 ml) was added followed by tert-butyl 2-((4-amino-3-methoxyphenyl)(methyl)amino)acetate (292 mg, 1.10 mmol). The resulting suspension was purged again and was heated at 100 °C for 1h30. After cooling, the mixture was filtered through a pad of Dicalite speed plus and washed with dichloromethane. The solvent were evaporated. PBO-01970-51-01 The crude product was purified by flash chromatography on silica gel (Merck cartridge SVF D26 - SI60 15-40µm - 30g) eluting with 0 up to 50% EtOAc in petroleum ether. Collected fractions were evaporated to afford tert-butyl 2-((4-(5-chloro-4-(8-fluoroimidazo[1,2-a]pyridin-3-yl)pyrimidin-2-ylamino)-3-methoxyphenyl)(methyl)amino)acetate (220 mg, 43.1 %) as a clear yellow solid. PBO-01970-51-02

Quelle

750 AstraZeneca ELN dataset