3-FLUORO-N-METHYLPYRID-2-YLMETHYLAMINE synthesis

Yield:884507-13-5 67%

Reaction Conditions:

Stage #1: 3-fluoropyridine-2-carbaldehyde;methylamine in methanol at 0; for 2 h;
Stage #2: with sodium tetrahydroborate in methanol at 0 - 20;

Steps:

1.1.15

Example 1.1.15: Synthesis of 1 -(3 -fluoropyridin-2-yl)-N-methylmethanamine[0294] Ti(0'PR)₄ (Commercial source: sigma-aldrich) (2.95 g, 10.4 mmol) was added with stirring to MeNH₂(Commercial source: sigma-aldrich) (2.0 M in MeOH, 12 ml, 23.7 mmol) under Ar. After 5 min. the aldehyde, 3-fluoropicolinaldehyde (1.0 g, 7.99 mmol)(Commercial source: sigma-aldrich) was added, and the solution was stirred for 2 h. The reaction was cooled to 0° C and the NaBH₄ (395 mg, 10.4 mmol) was added. The solution was stirred at 0° C to RT overnight. After quenching the reaction with water the mixture was filtered through celite to remove the white precipitate. Then MeOH was removed in vacuo. The residue was diluted with EtOAc. The resulting solution was washed with water (x3), brine (xl), and dried over Na₂S0₄. The inorganics were filtered off, and the solvent was removed in vacuo to give the crude product. Purification via column chromatography yielded the pure l-(3-fluoropyridin-2-yl)-N-methylmethanamine in 67% yield.

References:

WO2012/54510,2012,A1 Location in patent:Page/Page column 90