6-BROMO-N-METHYLPYRID-2-YLMETHYLAMINE synthesis

Yield:-

Reaction Conditions:

in tetrahydrofuran;dichloromethane at 20; for 18 h;

Steps:

3
To a solution of 6-bromopyridine-2-carbaldehyde (1.0Og, 5.38mmol) in CH₂Cl₂ (2OmL) was added methylamine (4.04mL, 2M/THF, 8.08mmol) then to the stirred solution was added sodium triacetoxyborohydride (1.37g, 6.46mmol). After stirring at rt for 18h, the mixture was partitioned between saturated aqueous NaHCO₃ (5OmL) and CH₂Cl₂ (10OmL). The layers were separated then the aqueous extracted with CH₂Cl₂ (2x30mL). The combined organics were washed with brine (5OmL), dried (MgSO₄), filtered and concentrated in vacuo. Purification via flash column chromatography (5%MeOH / CH₂Cl₂) afforded the desired compound: δ_H (CDCl₃): 2.49 (3H, s), 3.86 (2H, s), 7.31 (IH, d), 7.38 (IH, d), 7.53 (IH, t).

References:

PROSIDION LTD. WO2006/70208, 2006, A1 Location in patent:Page/Page column 18