Isopropanol → HCID 57968821, compound

To a solution of propan-2-ol (2.94 mL, 39.26 mmol) in DMF (15 mL) at 0° C. was added sodium hydride (95% in mineral oil, 0.94 g, 39.26 mmol) in portions and stirred for 1 h at room temperature. This mixture was slowly added to a solution of 2,6-dichloro-nicotinamide (5.0 g, 26.17 mmol) in DMF (25 mL) at 0° C. The reaction mixture was stirred at room temperature overnight. DMF was removed under reduced pressure, and the resulting mixture was diluted with EtOAc (50 mL), washed with water (2×20 mL) and brine (2×10 mL) solution, dried over anhydrous Na2SO4, filtered, and concentrated to give yellow oil. Purification was accomplished by flash chromatography on silica gel using 5-50% EtOAc/hexanes gradient elution to yield the title compound (2.94 g, 64%) as a white solid. 1H NMR (400 MHz, CDCl3) δ ppm 8.45 (d, J=8.2 Hz, 1 H), 7.73 (br. s., 1 H), 7.03 (d, J=7.8 Hz, 1 H), 5.84 (br. s., 1 H), 5.64-5.47 (m, 1 H), 1.45 (d, J=6.3 Hz, 6 H).

1. stirringThe reaction mixture was stirred at room temperature overnight
2. customDMF was removed under reduced pressure
3. additionthe resulting mixture was diluted with EtOAc (50 mL)
4. washwashed with water (2×20 mL) and brine (2×10 mL) solution
5. dry with materialdried over anhydrous Na2SO4
6. filtrationfiltered
7. concentrationconcentrated
8. customto give yellow oil
9. customPurification
10. washwas accomplished by flash chromatography on silica gel using 5-50% EtOAc/hexanes gradient elution

ORD record

ord-e9739f39f06f40e1aade7c9d47d309bc

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09012431B2