Reaktion #1922528

Reaktionsgleichung

4-iodo-2-methyl-pyridine

bis(pinacolato)diboron

potassium acetate

sodium carbonate

N-(3,5-bis-trifluoromethyl-benzyl)-6-iodo-N-methyl-4-o-tolyl-nicotinamide

N-(3,5-Bis-trifluoromethyl-benzyl)-6-iodo-N-methyl-4-o-tolyl-nicotinamide

→

title compound

Ausbeute 78.4%

2′-Methyl-4-o-tolyl-[2,4′]bipyridinyl-5-carboxylic acid (3,5-bis-trifluoromethyl-benzyl)-methyl-amide

Ausbeute 78.4%

Lösungsmittel

sodium bicarbonate

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas deoxygenated by three freeze-thaw cycles
2. 2
   TemperaturCooling to room temperature
3. 3
   workup.WAITThe reaction mixture was reheated to 80° C. for 1.5 h
4. 4
   TemperaturAfter cooling to room temperature the reaction mixture
5. 5
   Extraktionextracted with three portions of ethyl acetate
6. 6
   TrocknenThe combined organic extracts were dried with sodium sulfate
7. 7
   Filtrationfiltered
8. 8
   Einengenconcentrated
9. 9
   SonstigeDrying in high vacuo at 50° C.

Vorschrift

A mixture of 300 mg (1.37 mmol) 4-iodo-2-methyl-pyridine, 383 mg (1.51 mmol) bis(pinacolato)diboron and 403 mg (4.11 mmol) potassium acetate in 8.5 ml N,N-dimethylformamide was deoxygenated by three freeze-thaw cycles. After addition of 112 mg (0.137 mmol) dichloro(1,1′-bis(diphenylphosphino)ferrocene)palladium(II) dichloromethane adduct the reaction mixture was stirred at 80° C. for 3 h. Cooling to room temperature was followed by addition of 4 ml of a 2 M aqueous solution of sodium carbonate, 396 mg (0.685 mmol) N-(3,5-bis-trifluoromethyl-benzyl)-6-iodo-N-methyl-4-o-tolyl-nicotinamide (Example 4) and 56 mg (0.068 mmol) dichloro(1,1′-bis(diphenylphosphino)ferrocene)palladium(II) dichloromethane adduct. The reaction mixture was reheated to 80° C. for 1.5 h. After cooling to room temperature the reaction mixture was diluted with aqueous sodium bicarbonate solution and extracted with three portions of ethyl acetate. The combined organic extracts were dried with sodium sulfate, filtered and concentrated. Drying in high vacuo at 50° C. and flash column chromatography gave 292 mg (78%) of the title compound as a light brown solid.

Quelle