Chloromethyl Methyl Ether → 7-bromo-8-iodo-2-(methoxymethyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one

Temperature

20 °C

To a solution of 7-bromo-8-iodo-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one (1.0 g, 2.94 mmol) in DMF (10 mL) and N,N-diisopropylethylamine (2.6 mL, 14.7 mmol) at 20° C. was added chloromethyl methyl ether (473 mg, 5.9 mmol). The resulting reaction mixture was stirred for an additional 3 h at 20° C. and then quenched by addition of H2O (25 mL). The quenched reaction mixture was extracted with Et2O/EtOAc (2:1, 3×50 mL). The combined organic extract was washed with saturated aqueous NaHCO3 solution (30 mL), then brine (30 mL), dried over MgSO4, filtered and concentrated in vacuo to obtain the title compound as a light yellow solid (1.1 g, 2.86 mmol). MS: [M+H]+=384.0. 1H NMR (400 MHz, CDCl3) δ 3.46 (s, 3H), 5.34 (s, 2H), 6.68 (d, J=7.15 Hz, 1H), 7.65 (d, J=7.15 Hz, 1H).

1. customThe resulting reaction mixture
2. customquenched by addition of H2O (25 mL)
3. customThe quenched reaction mixture
4. extractionwas extracted with Et2O/EtOAc (2:1, 3×50 mL)
5. extractionThe combined organic extract
6. washwas washed with saturated aqueous NaHCO3 solution (30 mL)
7. dry with materialbrine (30 mL), dried over MgSO4
8. filtrationfiltered
9. concentrationconcentrated in vacuo

ORD record

ord-a74a663fb88b4fe697f9e4bc43c651bb

Source dataset

uspto-grants-2009_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07572808B2