Ethyl isothiocyanatoformate → 8-Bromo-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine

HRID 472360Notes

Reaction equation

[Br:1][C:2]1[C:3]([NH2:12])=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.C(OC([N:18]=[C:19]=S)=O)C.Cl.[NH2:22]O>>[Br:1][C:2]1[C:3]2[N:4]([N:22]=[C:19]([NH2:18])[N:12]=2)[CH:5]=[C:6]([C:8]([F:11])([F:9])[F:10])[CH:7]=1

Participants

Reactant 3

HCID 85320Ethyl isothiocyanatoformate

HCID 443297Hydroxyamine hydrochloride

HCID 130641553-Bromo-5-(trifluoromethyl)pyridin-2-amine

Product 1

HCID 674814698-Bromo-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine

Procedure

8-Bromo-6-trifluoromethyl-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine was prepared from 3-bromo-5-trifluoromethyl-pyridin-2-ylamine, ethoxycarbonylisothiocyanate, and hydroxylamine hydrochloride in a manner analogous to Steps 2a-b. 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 9.24 (s, 1H), 8.08 (s, 1H), 6.62 (bs, 2H). MS=282.9 (MH)+.

Sources & evidence

ORD record: ord-994dd7d9b7fe421f9f74733c9fd06c65
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08633173B2

Reaction notes

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