Sodium hydride → HCID 23362247, compound

A solution of trimethyl phosphonoacetate (5.5 mL) in dry tetrahydrofuran (25 mL) was added slowly to a cooled (cardice-acetone bath) suspension of sodium hydride (60% dispersion in oil, 1.34 g) in tetrahydrofuran (100 mL) under a nitrogen atmosphere such that the temperature of the reaction mixture remained between 0° C. and 10° C. during the addition. The resultant slurry was then cooled in an ice bath and stirred for 10 minutes prior to the addition of a solution of 4-[2-[N-methyl-N-(2-pyridyl)amino]ethoxy]benzaldehyde (8.3 g) (Eur. Patent. Appl., Publication No. 0306228) in tetrahydrofuran (100 mL). The mixture was stirred at room temperature for 20 hrs, then quenched with brine (10 mL) and concentrated in vacuo. The residue was suspended in brine (500 mL) and extracted with dichloromethane (3×300 mL), and the combined organic layers washed with water (1 L) and brine (1 L), dried (MgSO4) and evaporated. The residue was chromatographed on silica gel with 1% methanol in dichloromethane as eluent to afford the title compound, mp 93°-5° C. (dichloromethane-hexane).

1. temperaturea cooled
2. additionremained between 0° C. and 10° C. during the addition
3. temperatureThe resultant slurry was then cooled in an ice bath
4. stirringThe mixture was stirred at room temperature for 20 hrs
5. customquenched with brine (10 mL)
6. concentrationconcentrated in vacuo
7. extractionextracted with dichloromethane (3×300 mL)
8. washthe combined organic layers washed with water (1 L) and brine (1 L)
9. dry with materialdried (MgSO4)
10. customevaporated
11. customThe residue was chromatographed on silica gel with 1% methanol in dichloromethane as eluent

ORD record

ord-1ddddae0450c4727b5b371539cd88414

Source dataset

uspto-grants-1996_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05589492