Sodium hydride → HCID 131728135, compound

Temperature

100 °C

Tert-Butyl (2-hydroxyethyl)carbamate (8.88 g, 55.08 mmol) was added to a solution of NaH (55%, 55.08 mmol, washed twice with petroleum ether) in DMF (150 ml) at −10° C. and stirred for 10 mins. 2-Chloro-5-(trifluoromethyl)pyridine (10.0 g, 55.08 mmol) was added and the reaction mixture was stirred at rt for 3 days, heated to 100° C. and cooled to rt. The reaction mixture was evaporated, the residue was washed with isopropylether, and the solution was decanted from insoluble salts and concentrated. The residue was dissolved in EtOAc, washed twice with water, dried over MgSO4 and concentrated. Recrystallisation from isobutylethyl ether gave the title compound (6.2 g, 37%). 1H-NMR (500 MHz, CDCl3) δ 1.46 (s, 9H), 3.56 (br.m, 2H), 4.45 (t, 2H), 6.84 (d, 1H), 7.79 (dd, 1H), 8.44 (s, 1H.

1. washwashed twice with petroleum ether) in DMF (150 ml) at −10° C.
2. stirringthe reaction mixture was stirred at rt for 3 days
3. temperaturecooled to rt
4. customThe reaction mixture was evaporated
5. washthe residue was washed with isopropylether
6. customthe solution was decanted from insoluble salts
7. concentrationconcentrated
8. dissolutionThe residue was dissolved in EtOAc
9. washwashed twice with water
10. dry with materialdried over MgSO4
11. concentrationconcentrated
12. customRecrystallisation from isobutylethyl ether

ORD record

ord-1d67978da18d4d96a4903a5eb732ee84

Source dataset

uspto-grants-2011_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07960380B2