Реакция #168411

Уравнение реакции

{6-chloro-4-(5-chloropyridin-3-yl)-3-[(trans-4-methylcyclohexyl)methyl]-3H-imidazo[4,5-c]pyridin-2-yl}(3-fluoropyridin-2-yl)methanone

methyl magnesium bromide

→

(1RS)-1-{6-chloro-4-(5-chloropyridin-3-yl)-3-[(trans-4-methylcyclohexyl)methyl]-3H-imidazo[4,5-c]pyridin-2-yl}-1-(3-fluoropyridin-2-yl)ethanol

Растворители

THF

Условия реакции

Обработка

1. 1
   ДругоеThe reaction mixture was quenched with aqueous saturated NH4Cl solution (40 mL)
2. 2
   Экстракцияextracted with ethyl acetate (2×35 mL)
3. 3
   ПромывкаThe combined organic extracts were washed with brine (20 mL)
4. 4
   Сушкаdried over anhydrous Na2SO4
5. 5
   Фильтрацияfiltered
6. 6
   Концентрированиеconcentrated
7. 7
   ДругоеPurification of the residue on a silica gel column (0 to 100% EtOAc/hexanes)

Методика

To a stirred solution of {6-chloro-4-(5-chloropyridin-3-yl)-3-[(trans-4-methylcyclohexyl)methyl]-3H-imidazo[4,5-c]pyridin-2-yl}(3-fluoropyridin-2-yl)methanone (618 mg, 1.24 mmol) in THF (10 mL) was added methyl magnesium bromide (3 M in diethyl ether, 0.82 mL, 2.46 mmol) at −78° C., and the reaction mixture was stirred for 2 hours. The reaction mixture was quenched with aqueous saturated NH4Cl solution (40 mL) and extracted with ethyl acetate (2×35 mL). The combined organic extracts were washed with brine (20 mL), dried over anhydrous Na2SO4, filtered, and concentrated. Purification of the residue on a silica gel column (0 to 100% EtOAc/hexanes) afforded (1RS)-1-{6-chloro-4-(5-chloropyridin-3-yl)-3-[(trans-4-methylcyclohexyl)methyl]-3H-imidazo[4,5-c]pyridin-2-yl}-1-(3-fluoropyridin-2-yl)ethanol. MS APCl calcd. for C26H26Cl2FN5O [M+H]+ 514. found 514.

Источник