Hexachloroethane → HCID 66653381, compound

To a cooled (0° C.) suspension of commercially available 4-hydroxy-3-amino-pyridine 14 (4 g, 36 mmol) in DCM (200 ml) were added triethyl amine (6.3 ml, 1.25 eq) and a solution of 4-bromo-benzoyl chloride (15, Rb=H, 8 g, 36 mmol, 1 eq, 0.3M in DCM). The reaction mixture was allowed to reach room temperature and the mixture was stirred for 16 hrs. The mixture was filtered, washed with DCM and ether to furnish crude 16 (Rb=H) as a solid material which was used in the next step without further purification. Hexachloroethane (10.2 g, 43 mmol, 2.5 eq) was dissolved in DCM (150 ml) and triphenyl phosphine (13.56 g, 51.69 mmol, 3 eq) and triethyl amine (19.2 ml, 137.8 mmol, 8 eq) was added. The mixture was stirred for minutes at room temperature and crude compound 16 (Rb=H) was added slowly in 5 equal portions. The mixture was stirred at room temperature for 64 hrs after which time TLC analysis (DCM/MeOH, 97/3, v/v, Rf 0.3) revealed complete reaction. The solution was concentrated and the residue was suspended in DCM. The mixture was filtered and the residue washed with DCM and diethyl ether to give crude 17 (Rb=H) which was used in the next step without further purification.

1. temperatureTo a cooled
2. customto reach room temperature
3. filtrationThe mixture was filtered
4. washwashed with DCM and ether
5. customto furnish crude 16 (Rb=H) as a solid material which
6. customwas used in the next step without further purification
7. stirringThe mixture was stirred for minutes at room temperature
8. customreaction
9. concentrationThe solution was concentrated
10. filtrationThe mixture was filtered
11. washthe residue washed with DCM and diethyl ether
12. customto give crude 17 (Rb=H) which
13. customwas used in the next step without further purification

ORD record

ord-4349078c14994d8f9de56490a11af93b

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08796262B2