Reaktion #160922

Reaktionsgleichung

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

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

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title compound

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

Lösungsmittel

EtOAc

DMSO

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe vial was sealed
2. 2
   TemperaturAfter cooling to RT
3. 3
   Waschenwashed with brine
4. 4
   Trocknendried over Na2SO4
5. 5
   Sonstigethe solvent was evaporated off under reduced pressure
6. 6
   Sonstigeto give the crude product which
7. 7
   Sonstigewas purified by flash chromatography (RediSep® Silica gel column, n-heptane/EtOAc from 10% to 50% EtOAc)

Vorschrift

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]−.

Quelle