4-Bromo-2-furaldehyde → 7-Bromo-2-(4-bromo-furan-2-yl)-[1,2,4]triazolo[1,5-a]pyridin-5-ylamine

Reaction equation

[Br:1][C:2]1[CH:7]=[C:6]([NH2:8])[N:5]=[C:4]([NH2:9])[CH:3]=1.C1(C)C=C(C)C=C(C)C=1S(O[NH2:22])(=O)=O.[Br:24][C:25]1[CH:26]=[C:27]([O:30][CH:31]=1)[CH:28]=O>>[Br:1][C:2]1[CH:7]=[C:6]([NH2:8])[N:5]2[N:22]=[C:28]([C:27]3[O:30][CH:31]=[C:25]([Br:24])[CH:26]=3)[N:9]=[C:4]2[CH:3]=1

Participants

Reactant 3

HCID 27570104-Bromo-2-furaldehyde

HCID 114353934-Bromo-2,6-diaminopyridine

HCID 11830845O-(2,4,6-Trimethylbenzenesulfonyl)hydroxylamine

Product 1

HCID 183136207-Bromo-2-(4-bromo-furan-2-yl)-[1,2,4]triazolo[1,5-a]pyridin-5-ylamine

Procedure

The title compound, MS m/e (%): 359 (M++1, 100), was prepared in accordance with the general method of example 63 from 4-bromo-pyridine-2,6-diamine, O-mesitylene-sulfonylhydroxylamine, and 4-bromo-furfural. The purification was performed with reversed phase HPLC eluting with an acetonitrile/water gradient.

Sources & evidence

ORD record: ord-1f1fcf05d527464a9e4a53ba3b218a8f
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06355653B1

Reaction notes

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