Benzonitrile → 7-Bromo-2-phenyl-[1,2,4]triazolo[1,5-A]pyridine

HRID 517640

Reaction equation

[NH2:1][C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[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:6]1[CH:5]=[CH:4][N:3]2[N:31]=[C:24]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[N:1]=[C:2]2[CH:7]=1

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of 2-amino-4-bromopyridine (5.00 g, 28.9 mmol), copper (I) bromide (207 mg, 1.44 mmol), 1,10-phenanthroline monohydrate (289 mg, 1.44 mmol) and benzonitrile (65 mL) was heated in a 100-mL 4-necked flask to 130° C. During 23 h a gentle flow of air was bubbled through the reaction mixture (>99% conversion, HPLC method cf. example 1.3). The dark brown suspension was then cooled to 0-5° C. and filtered. The filter cake was washed with TBME (50 mL) and dried to yield crude 7-bromo-2-phenyl-[1,2,4]triazolo[1,5-a]pyridine (6.13 g, 75%) as a green solid with 97.1% purity (HPLC area-%, HPLC method cf. example 1.3).

Workup

customDuring 23 h a gentle flow of air was bubbled through the reaction mixture (>99% conversion, HPLC method cf. example 1.3)
temperatureThe dark brown suspension was then cooled to 0-5° C.
filtrationfiltered
washThe filter cake was washed with TBME (50 mL)
customdried

Sources & evidence

ORD record: ord-85c3bd2f6adb41e7a0d42d2c46ee44a1
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115130B2

Linked notes

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