تفاعل #160922

معادلة التفاعل

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

المذيبات

EtOAc

DMSO

ظروف التفاعل

المعالجة

1. 1
   أخرىThe vial was sealed
2. 2
   درجة الحرارةAfter cooling to RT
3. 3
   غسيلwashed with brine
4. 4
   تجفيفdried over Na2SO4
5. 5
   أخرىthe solvent was evaporated off under reduced pressure
6. 6
   أخرىto give the crude product which
7. 7
   أخرىwas purified by flash chromatography (RediSep® Silica gel column, n-heptane/EtOAc from 10% to 50% EtOAc)

الإجراء التجريبي

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]−.

المصدر