Dimethyl Sulfoxide → HCID 22938350, compound

A solution of 2-(4-fluorobenzoyl)-3-propoxypyridine (4.46 g) and sodium azide (3.34 g) in. DMSO (50 ml) was stirred for 22 hours at 90° C. To the reaction mixture was added water, and the mixture was extracted with diethylether. The organic layer was washed with saturated brine, dried over magnesium sulfate and concentrated under reduced pressure, and a solution of the residue (4.8 g) in THF (50 ml) was added dropwise to a suspension of aluminum lithium hydride (1.3 g) in. THF (40 ml) at 0° C. The mixture was stirred at room temperature for 30 minutes, water (1.3 ml), 15% aqueous solution of sodium hydroxide (1.3 ml) and water (3.9 ml) were sequentially and slowly added dropwise to the solution at 0° C. The mixture was stirred at room temperature for 2 hours, magnesium sulfate was added to the mixture, and the precipitates were removed by filtration (Celite). The reaction mixture was concentrated under reduced pressure, and the residue was recrystallized from ethyl acetate to give (4-aminophenyl)(3-propoxypyridin-2-yl)methanol (2.82 g) as pale yellow crystals.

1. extractionthe mixture was extracted with diethylether
2. washThe organic layer was washed with saturated brine
3. dry with materialdried over magnesium sulfate
4. concentrationconcentrated under reduced pressure
5. additiona solution of the residue (4.8 g) in THF (50 ml) was added dropwise to a suspension of aluminum lithium hydride (1.3 g) in
6. customat 0° C
7. additionslowly added dropwise to the solution at 0° C
8. stirringThe mixture was stirred at room temperature for 2 hours
9. additionmagnesium sulfate was added to the mixture
10. customthe precipitates were removed by filtration (Celite)
11. concentrationThe reaction mixture was concentrated under reduced pressure
12. customthe residue was recrystallized from ethyl acetate

ORD record

ord-e9c7cf1dce374e60a0ccdcb90cccebb1

Source dataset

uspto-grants-2007_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07262185B2