Ethanamine, 2,2,2-trifluoro- → HCID 59320965, compound

Temperature

60 °C

A solution of 5-bromo-pyridin-3-ylamine (1.73 g, 10 mmol) and 4-nitrophenyl chloroformate (2.2 g, 11 mmol) in dry THF (40 ml) was stirred and heated at 60° C. under N2 for 3 hours. After cooling to RT, DIPEA (5.2 ml, 30 mmol) and 2,2,2-trifluoroethylamine (1.6 ml, 20 mmol) were added and the solution was stirred at RT for 16 hours. The volatiles were removed in vacuo and the residue was partitioned between EtOAc and 1N NaOH. The organic layer was washed with H2O (×1) and brine (×1), then dried (MgSO4), filtered and evaporated. The residue was triturated with CH2Cl2. The solid was collected by filtration, washed with Et2O and dried under vacuum to give the title compound (1.7 g) as a colourless solid. 1H NMR (400 MHz, DMSO-d6): 9.18 (1H, s), 8.49 (1H, d), 8.28 (1H, d), 8.25 (1H, t), 7.06 (1H, t), 3.99-3.88 (2H, m).

1. temperatureAfter cooling to RT
2. customThe volatiles were removed in vacuo
3. customthe residue was partitioned between EtOAc and 1N NaOH
4. washThe organic layer was washed with H2O (×1) and brine (×1)
5. dry with materialdried (MgSO4)
6. filtrationfiltered
7. customevaporated
8. customThe residue was triturated with CH2Cl2
9. filtrationThe solid was collected by filtration
10. washwashed with Et2O
11. customdried under vacuum

ORD record

ord-cea0de205e0f4bd0ac5617652aeff093

Source dataset

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08895745B2