Diphenyl Ether → 8-Bromo-7-methoxy-1,6-naphthyridin-4(1H)-one
Reaction equation
[Br:1][C:2]1[C:3]([O:20][CH3:21])=[N:4][CH:5]=[CH:6][C:7]=1[NH:8][CH:9]=[C:10]1[C:15](=[O:16])OC(C)(C)OC1=O.C1(OC2C=CC=CC=2)C=CC=CC=1>CCCCCC>[Br:1][C:2]1[C:3]([O:20][CH3:21])=[N:4][CH:5]=[C:6]2[C:7]=1[NH:8][CH:9]=[CH:10][C:15]2=[O:16]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 250 °C
Procedure
A two neck round bottomed flask equipped with an air condenser was charged with 5-[(3-Bromo-2-methoxy-pyridin-4-ylamino)-methylene]-2,2-dimethyl-[1,3]dioxane-4,6-dione (23 g, 64 mmol) and diphenyl ether (230 mL). The reaction mixture was heated at 250° C. for 30 min under nitrogen atmosphere after which it was cooled to RT, diluted with hexane and filtered to obtain a dark solid. The crude product was refluxed in hexane for 30 min and filtered to obtained 8-Bromo-7-methoxy-1H-[1,6]naphthyridin-4-one as a brown solid.
Workup
- customA two neck round bottomed flask equipped with an air condenser
- temperaturewas cooled to RT
- filtrationfiltered
- customto obtain a dark solid
- filtrationfiltered
Sources & evidence
- ORD record
- ord-adf9a558e4ab4e8da6cde6b85ce7e605
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08524900B2
Reaction notes
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