Ammonia → HCID 178419419, compound

HRID 910246Notes

Reaction equation

[NH2:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][C:5]([Br:11])=[CH:4][N:3]=1.[O:12]1[C:16]([C:17]2[CH:24]=[CH:23][C:20]([CH:21]=O)=[CH:19][CH:18]=2)=[CH:15][N:14]=[CH:13]1.S(S([O-])=O)([O-])=O.[Na+].[Na+].N>CS(C)=O.O.C(O)C>[Br:11][C:5]1[CH:6]=[C:7]2[N:8]=[C:21]([C:20]3[CH:19]=[CH:18][C:17]([C:16]4[O:12][CH:13]=[N:14][CH:15]=4)=[CH:24][CH:23]=3)[NH:1][C:2]2=[N:3][CH:4]=1

Participants

Conditions

Temperature: 80 °C

Procedure

2-Amino-5-bromo-3-nitropyridine (218 mg) and 4-(1,3-oxazol-5-yl)benzaldehyde (173 mg) were suspended in dimethylsulfoxide (2 mL), followed by stirring at 80° C. for 20 minutes. Ethanol (4 mL) and 1M aqueous sodium hydrosulfite solution (3 mL) were added to the solution, followed by refluxing under heating for 15 hours. After the reaction mixture had been left to cool, water (20 mL) and concentrated aqueous ammonia solution (500 μL) were added thereto, and the precipitated solid was recovered through filtration, followed by washing with water and drying under reduced pressure, to thereby yield a 1:1 mixture (258 mg) of 5-[4-(6-bromo-3H-imidazo[4,5-b]pyridin-2-yl)phenyl]-1,3-oxazole and 5-[4-(6-bromo-1H-imidazo[4,5-b]pyridin-2-yl)phenyl]-1,3-oxazole.

Workup

temperatureby refluxing
temperatureunder heating for 15 hours
waitAfter the reaction mixture had been left
temperatureto cool
filtrationthe precipitated solid was recovered through filtration
washby washing with water
customdrying under reduced pressure

Sources & evidence

ORD record: ord-74ef4fcbb4b241eba2092dfdeae44379
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08022075B2

Reaction notes

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