Benzoyl chloride → Methyl 6-fluoro-2-phenyl-[1,2,4]triazolo[1,5-a]pyridine-7-carboxylate

HRID 1802183Notes

Reaction equation

C[C:2]1[CH:7]=[C:6](C)[CH:5]=[C:4]([CH3:9])[C:3]=1S([O-])(=O)=O.[NH2:14][N+:15]1[CH:20]=[C:19]([F:21])[C:18]([C:22]([O:24][CH3:25])=[O:23])=[CH:17][C:16]=1[NH2:26].C(Cl)(=O)C1C=CC=CC=1>N1C=CC=CC=1>[F:21][C:19]1[C:18]([C:22]([O:24][CH3:25])=[O:23])=[CH:17][C:16]2[N:15]([N:14]=[C:9]([C:4]3[CH:3]=[CH:2][CH:7]=[CH:6][CH:5]=3)[N:26]=2)[CH:20]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 1,2-diamino-5-fluoro-4-(methoxycarbonyl)pyridinium 2,4,6-trimethylbenzenesulfonate (1.719 g, 4.46 mmol) and benzoyl chloride (1.03 ml, 8.92 mmol) in pyridine (12 ml) is stirred for 20 hours at 100° C. The solvent is evaporated and the residue stirred for 2.5 hours with sat. aqueous ammoniumchloride solution while neutralizing to pH 6-7 with sat. aqueous sodium bicarbonate solution. The solid is collected by filtration, washed with water and dried affording methyl 6-fluoro-2-phenyl-[1,2,4]triazolo[1,5-a]pyridine-7-carboxylate (603 mg, 49.8%) as a light brown solid. Mp.: 162-8° C. MS: m/z=272.2 (M+H+).

Workup

customThe solvent is evaporated
stirringthe residue stirred for 2.5 hours with sat. aqueous ammoniumchloride solution
filtrationThe solid is collected by filtration
washwashed with water
customdried

Sources & evidence

ORD record: ord-6d8b2ad8f8de4a489de97708bd04c9ff
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08349824B2

Reaction notes

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