HCID 14503897, compound → HCID 42645907, compound

Temperature

-78 °C

A 3-L four neck round-bottom flask was purged and maintained with a nitrogen atmosphere and a solution of phenyl 4-methoxy-2-methylpyridine-1(2H)-carboxylate (454.1, 70.0 g, 285 mmol, 1.00 equiv) in tetrahydrofuran (1.2 L) was added. The solution was cooled to −78° C. then potassium tert-butoxide (128 g, 1.14 mol, 4.00 equiv) was added portion-wise. The resulting mixture was stirred at 10-15° C. for 20 h then concentrated in vacuo. The residue was dissolved in EtOAc (1.5 L), then carefully quenched with ice water (200 mL). The layers were separated and the aqueous was extracted with additional ethyl acetate (100 mL). The combined organics was washed with aqueous sodium hydroxide (1.5 M, 3×100 mL), aqueous hydrochloric acid (1 M, 2×100 mL), and brine (200 mL), dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (ethyl acetate/petroleum ether, 1:200-1:20) as the eluent to obtain the title compound as a light yellow oil (31.0 g, 51%).

1. customA 3-L four neck round-bottom flask was purged
2. temperaturemaintained with a nitrogen atmosphere
3. concentrationthen concentrated in vacuo
4. dissolutionThe residue was dissolved in EtOAc (1.5 L)
5. customcarefully quenched with ice water (200 mL)
6. customThe layers were separated
7. extractionthe aqueous was extracted with additional ethyl acetate (100 mL)
8. washThe combined organics was washed with aqueous sodium hydroxide (1.5 M, 3×100 mL), aqueous hydrochloric acid (1 M, 2×100 mL), and brine (200 mL)
9. dry with materialdried (Na2SO4)
10. filtrationfiltered
11. concentrationconcentrated in vacuo
12. customThe residue was purified by silica gel chromatography (ethyl acetate/petroleum ether, 1:200-1:20) as the eluent

ORD record

ord-00f358ad43d24d2e8f306b124e30b60b

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08871790B2