Реакция #168410

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)methanol

Dess-Martin periodinane

→

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

Растворители

dichloromethane

dichloromethane

Условия реакции

Обработка

1. 1
   ДругоеThen reaction
2. 2
   Другоеquenched with aqueous saturated NaHCO3 solution (40 mL)
3. 3
   Экстракцияextracted with dichloromethane (2×30 mL)
4. 4
   ПромывкаThe combined organic extracts were washed with brine (10 mL)
5. 5
   Сушкаdried over anhydrous Na2SO4
6. 6
   Фильтрацияfiltered
7. 7
   Концентрированиеconcentrated
8. 8
   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)methanol (807 mg, 1.61 mmol) in dichloromethane (15 mL) was added Dess-Martin periodinane (2.7 g, 6.45 mmoL) at 0° C. Then reaction was gradually warmed to room temperature and stirred for 2 hours. The reaction mixture was diluted with dichloromethane (15 mL), quenched with aqueous saturated NaHCO3 solution (40 mL), and extracted with dichloromethane (2×30 mL). The combined organic extracts were washed with brine (10 mL), dried over anhydrous Na2SO4, filtered, and concentrated. Purification of the residue on a silica gel column (0 to 100% EtOAc/hexanes) afforded {6-chloro-4-(5-chloropyridin-3-yl)-3-[(trans-4-methylcyclohexyl)methyl]-3H-imidazo[4,5-d]pyridin-2-yl}(3-fluoropyridin-2-yl)methanone. MS APCl calcd. for C25H22Cl2FN5O [M+H]+ 498. found 498.

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