反応 #619038

反応方程式

intermediate 11

1-(3-fluorobenzyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Intermediate 66R

tert-butyl 4-(3-fluoro-5-(3-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)pyridin-2-yl)piperazine-1-carboxylate

1-(3-fluorobenzyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

sodium carbonate

tert-butyl 4-(3-fluoro-5-(3-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)pyridin-2-yl)piperazine-1-carboxylate

→

titled compound

収率 88.0%

tert-butyl 4-(3-fluoro-5-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)pyridin-2-yl)piperazine-1-carboxylate

収率 88.0%

溶媒

toluene ethanol water

反応条件

後処理

1. 1
   その他reaction conditions

実験手順

Using similar reaction conditions as described in step-ii of example-1, tert-butyl 4-(3-fluoro-5-(3-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)pyridin-2-yl)piperazine-1-carboxylate (Intermediate 66R) (170 mg, 0.251 mmol) was coupled with 1-(3-fluorobenzyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (intermediate 11) (113 mg, 0.376 mmol) using sodium carbonate (80 mg, 0.753 mmol) and Pd(dppf)Cl2 (9.7 mg, 0.012 mmol) in toluene/ethanol/water (20/10/4 mL) to afford 160 mg (88% yield) of the titled compound after purification by column (Silica gel 60/120) using 37% ethyl acetate in hexane as eluent. MS: m/z=726.3 (M+1).

出典