Methylamine → 1-(6-Bromopyridin-2-yl)-N-methylmethanamine

Participants

Reaction Steps

To a solution of 6-bromopyridine-2-carbaldehyde (1.00 g, 5.38 mmol) in CH2Cl2 (20 mL) was added methylamine (4.04 mL, 2M/THF, 8.08 mmol) then to the stirred solution was added sodium triacetoxyborohydride (1.37 g, 6.46 mmol). After stirring at rt for 18 h, the mixture was partitioned between saturated aqueous NaHCO3 (50 mL) and CH2Cl2 (100 mL). The layers were separated then the aqueous extracted with CH2Cl2 (2×30 mL). The combined organics were washed with brine (50 mL), dried (MgSO4), filtered and concentrated in vacuo. Purification via flash column chromatography (5% MeOH/CH2Cl2) afforded the desired compound: δH (CDCl3): 2.49 (3H, s), 3.86 (2H, s), 7.31 (1H, d), 7.38 (1H, d), 7.53 (1H, t).

Provenance & Evidence