Imidazole → HCID 57809003, compound

To a solution of (2-chloropyridin-3-yl)methanol (3.4 g, 23.7 mmol) in 50 mL of dichloromethane was added imidazole (2.4 g, 35.3 mmol) and tert-butyldimethylsilyl chloride (4.3 g, 28.5 mmol) at RT. The mixture was stirred at RT for 60 min, and then diluted with 100 mL of hexanes. The white solid was filtered off, and the filtrate was concentrated under reduced pressure. Additional solid was removed by triturating with 5% ethyl acetate in hexanes to provide a pale yellow oil. The pale yellow oil was dissolved in 40 mL of dioxane and then hydrazine (7.5 mL, 238.7 mmol) was added. The resulting mixture was heated to reflux for 36 h. After this time, the mixture was cooled to RT, and the solvent was removed in vacuo to provide a residue. The residue was diluted with ethyl acetate, washed with water, dried over Na2SO4 and concentrated under reduced pressure to give the title compound (4.7 g, 78%) as a brown oil. HPLC Rt (Method A): 2.42 min. LC/MS (m/z)=254 (M+H)+.

1. filtrationThe white solid was filtered off
2. concentrationthe filtrate was concentrated under reduced pressure
3. customAdditional solid was removed
4. customby triturating with 5% ethyl acetate in hexanes
5. customto provide a pale yellow oil
6. temperatureThe resulting mixture was heated
7. temperatureto reflux for 36 h
8. temperatureAfter this time, the mixture was cooled to RT
9. customthe solvent was removed in vacuo
10. customto provide a residue
11. washwashed with water
12. dry with materialdried over Na2SO4
13. concentrationconcentrated under reduced pressure

ORD record

ord-c48515b12ed54db693fc5c1aade16ec6

Source dataset

uspto-grants-2009_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07579360B2