Benzonitrile → 2-Phenyl[1,2,4]triazolo[1,5-a]pyridine

Temperature

130 °C

A mixture of 2-amino-pyridine (2.00 g, 21.0 mmol), copper (I) bromide (160 mg, 1.09 mmol), 1,10-phenanthroline monohydrate (225 mg, 1.12 mmol) and benzonitrile (25 mL) was heated in a 50-mL 3-necked flask to 130° C. During 27 h a gentle flow of (O2/N2 5:95) was bubbled through the reaction mixture (>99% conversion, HPLC method see below). The dark brown suspension was then cooled to 0-5° C. and filtered. The filtrate was evaporated at 60° C./0.1 mbar to dryness and the dark brown residue dissolved in DCM (30 mL). The organic solution was washed with water (30 mL), dried over sodium sulphate, filtered and evaporated to yield 6.07 g of crude 2-phenyl-[1,2,4]triazolo[1,5-a]pyridine containing approx. 4 g of residual benzonitrile.

1. customDuring 27 h a gentle flow of (O2/N2 5:95) was bubbled through the reaction mixture (>99% conversion, HPLC method see below)
2. temperatureThe dark brown suspension was then cooled to 0-5° C.
3. filtrationfiltered
4. customThe filtrate was evaporated at 60° C./0.1 mbar to dryness
5. dissolutionthe dark brown residue dissolved in DCM (30 mL)
6. washThe organic solution was washed with water (30 mL)
7. dry with materialdried over sodium sulphate
8. filtrationfiltered
9. customevaporated

ORD record

ord-0b8ce9f1f5ec4878bd9ba89c3ce94d5b

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09115130B2