Acetic Anhydride → (2-Chloro-5-(4-(4-morpholinyl)-6-quinolinyl)-3-pyridinyl)methyl acetate

Participants

Reaction Steps

(Some starting materials may be obtained from Adesis Inc., New Castle, Del.) A mixture of (2-chloro-5-(4-morpholinoquinolin-6-yl)pyridin-3-yl)methanol (63 mg, 177 μmol), Hunig's Base (300 μl, 1718 μmol), and Ac2O (17 μl, 177 μmol) in DCM (10 mL) was stirred at rt. A small amount of DMF (10 drops) was added. After 2 h, a tiny amount of DMAP was added. After an additional 1 h, the solvent was removed under vacuum and the residue was treated with water. The slurry was extracted with DCM containing MeOH (2%). The organic phase was dried over Na2SO4, concentrated, and purified on silica using 1% MeOH in DCM to give a film (70 mg). LCMS (ESI, pos. ion): calc'd for C21H20ClN3O3: 397.1; found: 398.1 (M+1). 1H NMR (400 MHz, TFA-CHLOROFORM-d) δ ppm 2.26 (s, 3 H) 3.97 (d, J=4.02 Hz, 4 H) 4.11 (d, J=4.52 Hz, 4 H) 5.39 (s, 2 H) 7.10 (d, J=7.03 Hz, 1 H) 8.10-8.19 (m, 1 H) 8.17-8.28 (m, 2 H) 8.33 (s, 1 H) 8.60 (d, J=6.52 Hz, 1 H) 8.91 (d, J=2.01 Hz, 1 H) 13.20 (s, 1 H)

Provenance & Evidence