2,3-Diaminopyridine → 5-bromo-3-(1H-imidazo[4,5-b]pyridin-2-yl)pyridin-2-ylamine

HRID 241412

Reaction equation

[NH2:1][C:2]1[N:10]=[CH:9][C:8]([Br:11])=[CH:7][C:3]=1[C:4](O)=O.[N:12]1[CH:17]=[CH:16][CH:15]=[C:14]([NH2:18])[C:13]=1[NH2:19].[OH-].[Na+]>O>[Br:11][C:8]1[CH:7]=[C:3]([C:4]2[NH:18][C:14]3[C:13]([N:19]=2)=[N:12][CH:17]=[CH:16][CH:15]=3)[C:2]([NH2:1])=[N:10][CH:9]=1

Participants

Conditions

Temperature: 160 °C

Procedure

50 mg (0.230 mmol) I) of 2-amino-5-bromonicotinic acid and 27.6 mg (0.253 mmol) of pyridine-2,3-diamine are added to 451.5 mg (5 mmol) of polyphosphoric acid, and the mixture is stirred at 160° C. for 4 days. The reaction mixture is cooled to room temperature, water is added, and the mixture is adjusted to pH 12 by means of 1N NaOH. The precipitate formed is filtered off with suction and dried, giving 5-bromo-3-(1H-imidazo[4,5-b]pyridin-2-yl)pyridin-2-ylamine.

Workup

temperatureThe reaction mixture is cooled to room temperature
customThe precipitate formed
filtrationis filtered off with suction
customdried

Sources & evidence

ORD record: ord-725e8d02c86f429892222bd9e70741e6
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08648201B2

Linked notes

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