Yield:73335-64-5 92.5%

Reaction Conditions:

with sodium cyanoborohydride;triethylamine in methanol at 0 - 20; for 1.5 h;

Steps:

1 Step 1

To stirred mixture of 5-bromonicotinaldehyde (LVII) (2.0 g, 10.75 mmol), methanamine hydrochloride (0.06 mL, 32.26 mmol) and TEA (6.74 mL, 48.38 mmol) in MeOH (20 mL) was added NaCNBH₃ (2.03g, 32.26mmol) at 0°C and the mixture was stirred for 30 min. to 1 h at room temperature. Reaction mixture was quenched with minimum amount of aqueous saturated ammonium chloride solution, concentrated under vacuum and the residue was adsorbed on silica gel, purified by chromatography (010% 7N NH3-MeOH/Chloroform) to obtain 1-(5- bromopyridin-3-yl)-N-methylmethanamine (LVIII) (2.0 g, 9.95 mmol, 92.5% yield) as an yellow syrup. ESIMS found for C7H9BrN2 m/z 201.0 (Br⁷⁹M+H).

References:

WO2019/241540,2019,A1 Location in patent:Paragraph 0367-0368