N-Methoxy-N-methylacetamide → HCID 19354338, compound

Temperature

0 °C

To a solution of N-(pyridin-2-yl)pivalamide (2.0 g, 11.22 mmoles) in THF at −78° C. was added 9.4 mL (2.1 eq) of n-BuLi. The resulting mixture was stirred at 0° C. for 3 hours. The reaction mixture was then cooled to −78° C. after which N-methoxy-N-methylacetamide (1.2 g, 1.1 eq) was added as a solution in THF. The resulting mixture was stirred at room temperature for 2 hours. It was then quenched into ice-H2O. The resulting mixture was extracted with CH2Cl2 (3×20 mL) and the combined organic extracts were washed with H2O (2×20 mL), brine (1×20 mL), then dried over MgSO4. Concentration and purification by MPLC gave N-(3-acetylpyridin-2-yl)pivalamide (1.62 g, 65%). Spectroscopic data: 1H NMR (300 MHz, CDCl3) δ ppm 1.36 (s, 9 H) 2.65 (s, 3 H) 7.09 (dd, J=7.76, 4.83 Hz, 1 H) 8.17 (dd, J=7.76, 1.90 Hz, 1 H) 8.64 (dd, J=4.69, 2.05 Hz, 1 H) 11.49 (br. s., 1 H).

1. stirringThe resulting mixture was stirred at room temperature for 2 hours
2. customIt was then quenched into ice-H2O
3. extractionThe resulting mixture was extracted with CH2Cl2 (3×20 mL)
4. washthe combined organic extracts were washed with H2O (2×20 mL), brine (1×20 mL)
5. dry with materialdried over MgSO4
6. concentrationConcentration and purification by MPLC

ORD record

ord-07226eedd8aa4557bba5c64424f1b159

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08507682B2