反応 #2358594

反応方程式

4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohex-3-enyl)morpholine

(R/S) 4-iodo-1-(oxan-2-yl)-1H-pyrazole-3-carbaldehyde

K3PO4

→

(R/S) 4-(4-morpholinocyclohex-1-enyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole-3-carbaldehyde

収率 81.1%

溶媒

ethylene glycol dimethyl ether

反応条件

後処理

1. 1
   温度The reaction was cooled to room temperature
2. 2
   濃縮concentrated under vacuum
3. 3
   その他The residue was purified on a silica gel column
4. 4
   洗浄eluted with 50-100% of ethyl acetate in petroleum ether

実験手順

A mixture of 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohex-3-enyl)morpholine (293 mg, 1.00 mmol, 1.00 equiv), (R/S) 4-iodo-1-(oxan-2-yl)-1H-pyrazole-3-carbaldehyde (306 mg, 1.00 mmol, 1.00 equiv), K3PO4 (640 mg, 3.02 mmol, 3.02 equiv) and Pd(dppf)Cl2 (65.1 mg, 0.10 mmol, 0.10 equiv) in ethylene glycol dimethyl ether (5 mL) was stirred under nitrogen at 85° C. for 12 h. The reaction was cooled to room temperature and concentrated under vacuum. The residue was purified on a silica gel column eluted with 50-100% of ethyl acetate in petroleum ether to give 280 mg (81%) of (R/S) 4-(4-morpholinocyclohex-1-enyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole-3-carbaldehyde as a brown oil. LCMS (method C, ESI): RT=0.70 min, m/z=346.2 [M+H]+.

出典