Dichloromethane → 1-Propargyl-3-methoxypyridine-2-one

Temperature

100 °C

To a stirring solution of 3-methoxy-2-pyridinone (1.00 g, 8.00 mmol) in DMF (25 mL), was added propargyl bromide (80 wt % solution in toluene, 1.5 equiv) and K2CO3 (3.313 g, 24 mmol). Reaction mixture was heated to 100° C. After overnight reaction, reaction mixture was partitioned between EtOAc (120 mL) and water (100 mL). Organic layer was separated and washed repeatedly with water (7×100 mL) and brine (1×60 mL). Organic layer was dried on Na2SO4 and evaporated under vacuo to yield dark brown crude product. Column chromatography using gradient CH2Cl2:Acetone (max 20%) gave pure 150 (0.79 g, 60%) as a slightly brownish solid. 1H NMR (CDCl3, 400 MHz) δ 2.36 (1H, t, J=2.8), 3.67 (3H, m), 4.66 (1H, d, J=2.8), 6.05 (1H, t, J=7.2), 6.50 (1H, dd, J=1.6, 7.2), 7.11 (1H, dd, J=1.6, 6.8); 13C NMR (CDCl3, 100 MHz) δ 37.2, 55.5, 74.6, 77.3, 104.8, 112.0, 126.3, 149.4, 157.1. HRMS (EI) calcd for C9H9NO2 [M]+ 163.0633. found 163.0636

1. customReaction mixture
2. customAfter overnight reaction, reaction mixture
3. customwas partitioned between EtOAc (120 mL) and water (100 mL)
4. customOrganic layer was separated
5. washwashed repeatedly with water (7×100 mL) and brine (1×60 mL)
6. customOrganic layer was dried on Na2SO4
7. customevaporated under vacuo
8. customto yield dark brown crude product

ORD record

ord-24ca005d30bf481182517071c8202e73

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08871728B2