Reaktion #627

Reaktionsgleichung

COc1ccc(Nc2cc(Cl)ccn

NCc1ccccc1

→

COc1ccc(Nc2cc(NCc3cc

Ausbeute 59.2%

Lösungsmittel

CC(=O)N(C)C

Reaktionsbedingungen

Vorschrift

Phenylmethanamine (50.2 mg, 0.47 mmol), 4-chloro-N-(4-methoxyphenyl)pyridin-2-amine (100 mg, 0.43 mmol) and sodium 2-methylpropan-2-olate (82 mg, 0.85 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 (28.4 mg, 0.05 mmol) and diacetoxypalladium (7.65 mg, 0.03 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-benzyl-N2-(4-methoxyphenyl)pyridine-2,4-diamine (77 mg, 59.2 %) as an off-white solid.

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