Potassium Carbonate → 6-Bromofuro[3,2-b]pyridine
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[O:10][C:9]([Si](C)(C)C)=[CH:8][C:5]2=[N:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+]>>[Br:1][C:2]1[CH:3]=[C:4]2[O:10][CH:9]=[CH:8][C:5]2=[N:6][CH:7]=1Participants
Procedure
6-Substituted-furo[3,2-b]pyridines of general formula (42), wherein Z is as defined in formula I, can be prepared as described in Scheme 8. 5-Bromo-3-hydroxypyridine can be treated with iodine and a base such as sodium carbonate to provide 5-bromo-3-hydroxy-2-iodopyridine. 5-Bromo-3-hydroxy-2-iodopyridine can be treated with. ethynyl(trimethyl)silane, a palladium catalyst and copper(I) iodide to provide 6-bromo-2-(trimethylsilyl)furo[3,2-b]pyridine. 6-Bromo-2-(trimethylsilyl)furo[3,2-b]pyridine can be treated with a base such as potassium carbonate to provide 6-bromo-furo[3,2-b]pyridine. 6-Bromo-furo[3,2-b]pyridine can be processed as described in previous Schemes, in particular Scheme 4, to provide 6-substituted-furo[3,2-b]pyridines of general formula (42).
Sources & evidence
- ORD record
- ord-0edc29ca16684b52bfec3655b2fca34d
- Source dataset
- uspto-grants-2008_02
- Patent number
- US07332504B2
Reaction notes
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