反応 #162091

反応方程式

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

溶媒

dimethylacetamide

反応条件

後処理

1. 1
   温度cooled to room temperature
2. 2
   ろ過The reaction mixture was filtered through celite
3. 3
   濃縮concentrated in vacuo
4. 4
   その他the resulting crude residue was purified by by preparatory HPLC (0.1% TFA-H2O/acetonitrile)

実験手順

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:

出典