3-Pyridinemethanamine → 5-bromo-3-methyl-N-(pyridin-3-ylmethyl)thiophene-2-carboxamide

To a stirred mixture of 5-bromo-3-methylthiophene-2-carboxylic acid (1.70 g, 7.69 mmol), 1-hydroxybenzotriazole (1.56 g, 11.54 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (2.21 g, 11.54 mmol) in anhydrous N,N-dimethylformamide (30 mL) was added N,N-diisopropylethylamine (4.10 mL, 23.54 mmol), followed by the addition of 3-(aminomethyl)pyridine (0.78 mL, 7.69 mmol). The resulting reaction mixture was stirred at ambient temperature for 16 h, and diluted with ethyl acetate (200 mL). The organic layer was washed with saturated aqueous sodium bicarbonate solution (3×100 mL) and water (100 mL), dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography eluted with 7% methanol in dichloromethane to afford 5-bromo-3-methyl-N-(pyridin-3-ylmethyl)thiophene-2-carboxamide as an off-white solid (1.92 g, 80%): MS (ES+) m/z 311.1 (M+1), 313.1 (M+1).

1. customThe resulting reaction mixture
2. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution (3×100 mL) and water (100 mL)
3. dry with materialdried over sodium sulfate
4. filtrationfiltered
5. concentrationconcentrated in vacuo
6. customThe residue was purified by column chromatography
7. washeluted with 7% methanol in dichloromethane

ORD record

ord-271e33b7250641ff928fc55543d0dd3c

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08258160B2