反応 #160922

反応方程式

6-chloro-5-iodo-N-(4-(trifluoromethoxy)phenyl)nicotinamide

4-fluoro-5-(tributylstannyl)-1H-pyrazole

→

title compound

6-Chloro-5-(4-fluoro-1H-pyrazol-5-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide

溶媒

EtOAc

DMSO

反応条件

後処理

1. 1
   その他The vial was sealed
2. 2
   温度After cooling to RT
3. 3
   洗浄washed with brine
4. 4
   乾燥dried over Na2SO4
5. 5
   その他the solvent was evaporated off under reduced pressure
6. 6
   その他to give the crude product which
7. 7
   その他was purified by flash chromatography (RediSep® Silica gel column, n-heptane/EtOAc from 10% to 50% EtOAc)

実験手順

Pd(Ph3P)4 (17.33 mg, 0.015 mmol) was added to solution of 6-chloro-5-iodo-N-(4-(trifluoromethoxy)phenyl)nicotinamide (Stage 4.2, 133 mg, 0.3 mmol) and 4-fluoro-5-(tributylstannyl)-1H-pyrazole (101 mg, 0.270 mmol) in DMSO (1 mL) in a vial under an argon atmosphere. The vial was sealed and the RM mixture was heated at 100° C. for 18 h. After cooling to RT, the RM was dissolved in EtOAc, washed with brine, dried over Na2SO4 and the solvent was evaporated off under reduced pressure to give the crude product which was purified by flash chromatography (RediSep® Silica gel column, n-heptane/EtOAc from 10% to 50% EtOAc) to afford the title compound as an off-white powder. HPLC (Condition 4) tR=5.5 min, UPLC-MS (Condition 3) tR=1.05 min, m/z=399.2 [M−H]−.

出典