Реакция #162091

Уравнение реакции

5-chloro-1-(p-tolylsulfonyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrolo[2,3-b]pyridine

1-((2-chloro-5-fluoropyrimidin-4-ylamino)methyl)cyclohexanol

14a

1-((2-chloro-5-fluoropyrimidin-4-ylamino)methyl)cyclohexanol

KOAc

→

14b

2-((2-(5-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-ylamino)methyl)cyclohexanol

Растворители

dimethylacetamide

Условия реакции

Обработка

1. 1
   Температураcooled to room temperature
2. 2
   ФильтрацияThe reaction mixture was filtered through celite
3. 3
   Концентрированиеconcentrated in vacuo
4. 4
   Другоеthe resulting crude residue was purified by by preparatory HPLC (0.1% TFA-H2O/acetonitrile)

Методика

To a degassed solution of 5-chloro-1-(p-tolylsulfonyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrolo[2,3-b]pyridine (0.15 g, 0.35 mmol), 1-((2-chloro-5-fluoropyrimidin-4-ylamino)methyl)cyclohexanol, 14a, (0.09 g, 0.35 mmol) and aqueous KOAc solution (1.04 mL of 1M solution, 1.04 mmol) in dimethylacetamide was added palladium triphenylphosphine (0.04 g, 0.03 mmol). The reaction mixture was heated at 140° C. in microwave for 15 min and then cooled to room temperature. The reaction mixture was filtered through celite, concentrated in vacuo, and the resulting crude residue was purified by by preparatory HPLC (0.1% TFA-H2O/acetonitrile) to afford the desired product, 14b:

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