Sodium hydride → HCID 178511711, compound

Temperature

60 °C

To a cooled (0° C.) 150 mL reaction tube equipped with reflux condenser and under a nitrogen atmosphere, were added trans-4-aminocyclohexanol (2.0 g, 17 mmol), NaH (2.08 g, 60% dispersion in mineral oil, 52.1 mmol), and DMF (25 mL) to give a colorless solution. After stirring for 1 h, 3-bromo-2-chloropyridine (3.34 g, 17.4 mmol) was added to the mixture And the resulting mixture heated at 60° Celsius for 5 h. After the starting material was consumed, the reaction was cooled to room temperature and quenched with H2O (2 mL). The reaction mixture was concentrated to dryness and the resultant residue purified by FCC to provide the title compound. 1H NMR (400 MHz, DMSO-d6) δ 8.11 (dd, J=4.8, 1.6, 1H), 7.98 (dd, J=7.7, 1.6, 1H), 6.89 (dd, J=7.7, 4.8, 1H), 4.92 (dd, J=9.4, 5.2, 1H), 2.98 (s, 1H), 2.05 (m, 2H), 1.95 (m, 2H), 1.53-1.38 (m, 4H)

1. temperatureTo a cooled
2. custom(0° C.) 150 mL reaction tube
3. customequipped
4. temperaturewith reflux condenser
5. customto give a colorless solution
6. customAfter the starting material was consumed
7. temperaturethe reaction was cooled to room temperature
8. customquenched with H2O (2 mL)
9. concentrationThe reaction mixture was concentrated to dryness
10. customthe resultant residue purified by FCC

ORD record

ord-04eb390446264f7ea2f947b02fdbd5fb

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09079866B2