Diisopropylethylamine → Ethyl 6-chloro-4-(methylamino)pyridine-3-carboxylate

Temperature

70 °C

To a solution of ethyl 4,6-dichloronicotinate (5.0 g, 22.7 mmol) in acetonitrile (50 mL) was added methylamine hydrochloride salt (1.84 g, 27.2 mmol) and diisopropylethylamine (14.6 g, 113.6 mmol), and the reaction mixture was heated at 70° C. overnight. LCMS showed the reaction was completed. The reaction was cooled to RT, quenched with water (50 mL) and extracted with ethyl acetate (3×100 mL). The organic layers were separated, combined, washed with water (50 mL) and brine (100 mL), dried over sodium sulfate, filtered, and concentrated to afford the title compound (4.7 g, crude), which was directly used in the next step without further purification. MS (ES+) C9H11ClN2O2 requires: 214, 216. found: 215, 217 [M+H]+.

1. temperatureThe reaction was cooled to RT
2. customquenched with water (50 mL)
3. extractionextracted with ethyl acetate (3×100 mL)
4. customThe organic layers were separated
5. washwashed with water (50 mL) and brine (100 mL)
6. dry with materialdried over sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated

ORD record

ord-ea531051c4f14212afe1aea289a5a8d1

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08802697B2