Triethylamine → 5-bromo-N,N-dimethylpicolinamide

Temperature

0 °C

5-Bromopyridine-2-carboxylic acid (20 g, 100 mmol, Frontier Scientific catalog# B1704) was stirred in methylene chloride (30 mL) and cooled to 0° C. 2.0 M oxalyl chloride in methylene chloride (100 mL) was added slowly, followed by N,N-dimethylformamide (0.8 mL). The mixture was stirred for 30 minutes at 0° C. and then room temperature overnight. The mixture was evaporated, redissolved in methylene chloride (130 mL) and was added slowly to a mixture of dimethylamine hydrochloride (9.8 g, 120 mmol) and triethylamine (56.1 mL, 400 mmol) in methylene chloride (130 mL) cooled to 0° C. The reaction mixture was stirred at room temperature for 2 hrs. This mixture was diluted with methylene chloride (200 mL) and washed with saturated sodium bicarbonate, brine, dried over sodium sulfate, filtered and evaporated. The product was purified by FCC on silica gel using ethyl acetate in hexanes (0-60%) gradient to give 5-bromo-N,N-dimethylpyridine-2-carboxamide, (22.0 g, 100%). LCMS calculated for C8H10BrN2O (M+H)+: m/z=229.0, 231.0; found: 228.9, 230.9.

1. customroom temperature overnight
2. customThe mixture was evaporated
3. dissolutionredissolved in methylene chloride (130 mL)
4. temperaturecooled to 0° C
5. stirringThe reaction mixture was stirred at room temperature for 2 hrs
6. washwashed with saturated sodium bicarbonate, brine
7. dry with materialdried over sodium sulfate
8. filtrationfiltered
9. customevaporated
10. customThe product was purified by FCC on silica gel

ORD record

ord-f3b478f77bab4c8b9b3ac9c4d1421743

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09199982B2