Diethyl Ether → HCID 57546048, compound

Temperature

0 °C

(±)-1-(5-Chloro-2-cyclopropyl-2H-indazol-7-yl)ethanol (240 mg, 1.01 mmol) was dissolved in methylene chloride (5 mL), cooled to 0° C. and treated with 1,8-diazabicyclo(5.4.0)undec-7-ene (31 μL, 0.2 mmol). The reaction was stirred for 10 min and treated with trichloroacetonitrile (1 mL, 10.1 mmol) dropwise over 10 min. The ice bath was removed and the reaction stirred at room temperature for 1 h and concentrated to give a dark brown solid. The crude product was treated with diethyl ether and stirred vigorously for 10 min. The resulting mixture was filtered through a pad of cotton and the ethereal concentrated to afford 365 mg (94%) as an oil. 1H-NMR (CDCl3, 300 MHz) δ 8.33 (s, 1H), 7.89 (s, 1H), 7.48 (m, 1H), 7.29 (m, 1H), 6.59 (q, J=6.6 Hz, 1H), 3.86-3.94 (m, 1H), 1.77 (d, J=6.6 Hz, 1H), 1.30-1.35 (m, 2H), 1.10-1.20 (m, 2H).

1. customThe ice bath was removed
2. stirringthe reaction stirred at room temperature for 1 h
3. concentrationconcentrated
4. customto give a dark brown solid
5. stirringstirred vigorously for 10 min
6. filtrationThe resulting mixture was filtered through a pad of cotton
7. concentrationthe ethereal concentrated
8. customto afford 365 mg (94%) as an oil

ORD record

ord-fc4eaa6b3a974be3bf68543bd73e2533

Source dataset

uspto-grants-2011_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08026257B2