Diisobutylaluminumhydride → 2-[4-(6-Chloropyridin-3-yl)-1H-1,2,3-triazol-1-yl]ethanol

Temperature

0 °C

Ethyl[4-(6-chloropyridin-3-yl)-1H-1,2,3-triazol-1-yl]acetate (150 mg, 0.56 mmol) (Example 413, Step 2) was taken up in THF (2.8 ml) and cooled to 0° C. Diisobutyl aluminum hydride (1.7 ml of 1.0M in hexanes, 1.7 mmol) was added dropwise over 15 minutes, and the reaction was maintained at 0° C. for 30 minutes. The reaction was allowed to warm to room temperature and maintained at room temperature for 20 hours. The mixture was then quenched with saturated aqueous potassium sodium tartrate and stirred for 2 hours. Ethyl acetate (10 mL) was added, and the mixture was stirred for 1 hour, after which product was extracted three times with ethyl acetate. The organic layers were combined, dried over anhydrous magnesium sulfate, filtered, and concentrated. The resulting crude product was purified by silica gel chromatography (0-5% methanol/ethyl acetate) to afford the title compound.

1. temperaturethe reaction was maintained at 0° C. for 30 minutes
2. temperatureto warm to room temperature
3. temperaturemaintained at room temperature for 20 hours
4. customThe mixture was then quenched with saturated aqueous potassium sodium tartrate
5. additionEthyl acetate (10 mL) was added
6. stirringthe mixture was stirred for 1 hour
7. extractionafter which product was extracted three times with ethyl acetate
8. dry with materialdried over anhydrous magnesium sulfate
9. filtrationfiltered
10. concentrationconcentrated
11. customThe resulting crude product was purified by silica gel chromatography (0-5% methanol/ethyl acetate)

ORD record

ord-b64187a80d824121b845bc7c60224680

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08367706B2