3-Fluorobenzylamine → 4-N-[(3-fluorophenyl)methyl]-2-N-phenylpyridine-2,4-diamine

Temperature

100 °C

(3-fluorophenyl)methanamine (67.3 mg, 0.54 mmol), 4-chloro-N- phenylpyridin-2-amine (100 mg, 0.49 mmol) and sodium 2-methylpropan-2-olate (94 mg, 0.98 mmol) were suspended in DMA (2 mL) and sealed into a microwave tube. Nitrogen was bubbled through the reaction mixture for 5 minutes. (R)-(-)-1-[(S)-2-(DICYCLOHEXYLPHOSPHINO)FERROCENYL]ETHYLDI-T-BUTYLPHOSPHINE (32.5 mg, 0.06 mmol) and diacetoxypalladium (8.78 mg, 0.04 mmol) were added to the reaction mixture and nitrogen was bubbled through the reaction mixture for a further 5 minutes. The reaction was heated thermally to 100 °C for 30 mins under nitrogen and cooled to RT. The reaction mixture was neutralised with HCl and purified by ion exchange chromatography, using a 20 g SCX column. The crude product was purified by flash silica chromatography, elution gradient 0 to 10% MeOH in DCM. Fractions containing product were evaporated to dryness to afford N4-(3-fluorobenzyl)-N2-phenylpyridine-2,4-diamine (84 mg, 58.6 %) as an off-white solid.

ORD record

ord-2ad8db0a7ea741b0a4428eec268f91fd

Source dataset

750 AstraZeneca ELN dataset

Original link

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