Triphenylphosphine → HCID 22000176, compound

Temperature

0 °C

3-Bromo-2-chloro-5-trifluoroacetamidopyridine (0.53 g, 1.75 mmol) and triphenylphosphine (550 mg, 2.10 mmol) in carbon tetrachloride (50 ml) was refluxed for 16 hrs and then cooled to 0° C. Aminoacetaldehyde diethyl acetal (0.25 ml, 1.72 mmol) was added and the mixture stirred at 0° C. for 1 hr, then at 22° C. for 2 hrs. After concentration in vacuo, acetic acid (4 ml) was added and the mixture refluxed for 7 hrs, then cooled. Ethyl acetate (20 ml) was added and the resulting solution was washed with sodium hydroxide solution (50 ml, 2M) and brine (50 ml) before being dried (MgSO4) and concentrated. The residue was purified by silica chromatography to give the product as yellow solid (104 mg).

1. waitat 22° C. for 2 hrs
2. concentrationAfter concentration in vacuo, acetic acid (4 ml)
3. additionwas added
4. temperaturethe mixture refluxed for 7 hrs
5. temperaturecooled
6. additionEthyl acetate (20 ml) was added
7. washthe resulting solution was washed with sodium hydroxide solution (50 ml, 2M) and brine (50 ml)
8. dry with materialbefore being dried (MgSO4)
9. concentrationconcentrated
10. customThe residue was purified by silica chromatography

ORD record

ord-27ba120b3a204ff787024be21ea36a89

Source dataset

uspto-grants-2001_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06225320B1