反応 #618808

反応方程式

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

sodium carbonate

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

intermediate 11

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

intermediate 67

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

→

titled compound

収率 93.3%

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

収率 93.3%

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-i of example-1, tert-butyl 4-(2-fluoro-4-(3-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperidine-1-carboxylate (intermediate 67) (250 mg, 0.370 mmol) was coupled with 1-(3-fluorobenzyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (intermediate 11) (168 mg, 0.555 mmol) using Pd(DPPF)Cl2 (14 mg, 0.018 mol) and sodium carbonate (118 mg, 1.110 mmol) in toluene/ethanol/water (5/5/1 ml) to afford 250 mg (93.2% yield) of the titled compound after column purification using 1% methanol in DCM as eluent. MS: m/z=724.4 (M+1).

出典