2,6-Difluorobenzylamine → 4-N-[(2,6-difluorophenyl)methyl]-2-N-phenylpyridine-2,4-diamine

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

4-chloro-N-phenylpyridin-2-amine (100 mg, 0.49 mmol), (2,6-difluorophenyl)methanamine (91 mg, 0.64 mmol), (R)-(-)-1-[(S)-2-(DICYCLOHEXYLPHOSPHINO)FERROCENYL]ETHYLDI-T-BUTYLPHOSPHINE (32.5 mg, 0.06 mmol),sodium 2-methylpropan-2-olate (94 mg, 0.98 mmol) and diacetoxypalladium (8.78 mg, 0.04 mmol) were suspended in DME (2.0 mL) and sealed into a microwave tube. The reaction was heated to 150 °C for 20 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 fractions were evaporated to dryness to afford crude product. The crude product was purified by preparative HPLC (Waters XBridge Prep C18 OBD column, 5µ silica, 50 mm diameter, 100 mm length), using decreasingly polar mixtures of water (containing 1% NH3) and MeCN as eluents. Fractions containing the desired compound were evaporated to dryness to afford N4-(2,6-difluorobenzyl)-N2-phenylpyridine-2,4-diamine (32.0 mg, 21.04 %) as a yellow gum.

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