Triethylamine → 2-Amino-5-bromopyridine-3-carboxamide

To an ice-cold suspension of 2-amino-5-bromo-nicotinic acid hydrobromide (5.11 g, 17.1 mmol) and ammonium chloride (9.15 g, 171 mmol) in dimethoxyethane (170 mL) was added Et3N (4.8 mL, 34.2 mmol). After 10 min, diethylphosphoryl cyanide was added dropwise and the cold bath removed. After 4 h, the solution was filtered and the filtrate concentrated. The resulting residue was partitioned between EtOAc and water. The organic layer was washed with satd NaHCO3 (2×) and satd NaCl, dried (Na2SO4) and concentrated under reduced pressure. The yellow solid was dissolved in EtOAc and then hexanes were added until precipitation occurred. The solid was collected by filtration and then triturated with EtOAc to give the title compound (1.62 g, 44%) as a yellow solid: 1H NMR (300 MHz, DMSO-d6) δ 8.13 (s, 2H), 8.04 (bs, 1H), 7.46 (bs, 1H), 7.37 (bs, 2H).

1. customthe cold bath removed
2. waitAfter 4 h
3. filtrationthe solution was filtered
4. concentrationthe filtrate concentrated
5. customThe resulting residue was partitioned between EtOAc and water
6. washThe organic layer was washed with satd NaHCO3 (2×) and satd NaCl
7. dry with materialdried (Na2SO4)
8. concentrationconcentrated under reduced pressure
9. dissolutionThe yellow solid was dissolved in EtOAc
10. additionhexanes were added until precipitation
11. filtrationThe solid was collected by filtration
12. customtriturated with EtOAc

ORD record

ord-04d50eb4ab964a50bb1183d8a4797978

Source dataset

uspto-grants-2011_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07879872B2