Benzonitrile → HCID 71680411, compound

HRID 517650Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.O.N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.[C:24](#[N:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>[Cu]Br>[Br:8][C:5]1[CH:6]=[CH:7][C:2]2[N:3]([N:31]=[C:24]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[N:1]=2)[CH:4]=1

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of 2-amino-5-bromopyridine (2.00 g, 11.6 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 24 h a gentle flow of (O2/N2 5:95) was bubbled through the reaction mixture (>97% conversion, HPLC method see below). The dark brown suspension was then cooled to 0-5° C. and filtered. The filter cake was washed with TBME (10 mL) and dried to yield crude 6-bromo-2-phenyl-[1,2,4]triazolo[1,5-a]pyridine (1.14 g, 36%) as a light brown solid with 99.7% purity (HPLC area-%, HPLC method see below).

Workup

customDuring 24 h a gentle flow of (O2/N2 5:95) was bubbled through the reaction mixture (>97% conversion, HPLC method see below)
temperatureThe dark brown suspension was then cooled to 0-5° C.
filtrationfiltered
washThe filter cake was washed with TBME (10 mL)
customdried

Sources & evidence

ORD record: ord-141a3e156c24414cb98eff3dc778be62
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115130B2

Reaction notes

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