Reaction #172

Reaction equation

CNC(=O)c1ccccc1Nc1cc

Cc1nn(C)cc1N

→

CNC(=O)c1ccccc1Nc1cc

Yield 33.7%

Solvents

COCCOC

Conditions

Procedure

Palladium(II) acetate (8.17 mg, 0.04 mmol), (R)-(-)-1-[(S)-2-(Dicyclohexylphosphino)ferrocenyl]ethyldi-t-butylphosphine (20.40 mg, 0.04 mmol), Sodium tert-butoxide (0.052 mL, 0.42 mmol), 1,3-dimethyl-1H-pyrazol-4-amine (40.5 mg, 0.36 mmol) and 2-(2-chloro-5-(trifluoromethyl)pyridin-4-ylamino)-N-methylbenzamide (100 mg, 0.30 mmol) were suspended in DME (2.5 mL) and sealed into a microwave tube. The reaction was heated to 150 °C for 30 minutes in the microwave reactor and cooled to RT. The crude product was purified by ion exchange chromatography, using an SCX column. The desired product was eluted from the column using 7M NH3/MeOH and pure fractions were evaporated to dryness to afford 2-(2-(1,3-dimethyl-1H-pyrazol-4-ylamino)-5-(trifluoromethyl)pyridin-4-ylamino)-N-methylbenzamide (41.3 mg, 33.7 %) as a orange gum. The sample was given to the purification group to be purified by preparative HPLC. Fractions containing the desired compound were evaporated to dryness to afford 2-(2-(1,3-dimethyl-1H-pyrazol-4-ylamino)-5-(trifluoromethyl)pyridin-4-ylamino)-N-methylbenzamide (41.3 mg, 33.7 %) as a yellow solid.

Source