Homoallyl bromide → 5-But-3-enyloxy-pyridine-2-carboxylic acid
Reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[CH:8][C:9]([C:12]([OH:14])=[O:13])=[N:10][CH:11]=2)[CH2:3][CH2:2]1.COC(C1C=CC(O)=CN=1)=O.BrCCC=C.COC(C1C=CC(OCCC=C)=CN=1)=O>>[CH2:4]([O:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]([OH:14])=[O:13])=[N:10][CH:11]=1)[CH2:1][CH:2]=[CH2:3]Participants
5
Procedure
The 5-but-3-enyloxy-pyridine-2-carboxylic acid was prepared in a reaction sequence analogous to that in example 60 for the preparation of the 5-cyclopropylmethoxy-pyridine-2-carboxylic acid: Alkylation of the 5-hydroxy-pyridine-2-carboxylic acid methyl ester with 4-bromo-1-butene and hydrolysis of the 5-but-3-enyloxy-pyridine-2-carboxylic acid methyl ester yielded the 5-but-3-enyloxy-pyridine-2-carboxylic acid as a light yellow solid. Mass (calculated) C10H11NO3 [193.201]; (found) [M+H]+=194.
Workup
- customThe 5-but-3-enyloxy-pyridine-2-carboxylic acid was prepared in a reaction sequence analogous to that in example 60
Sources & evidence
- ORD record
- ord-30b616b5ee2441909196d41d2c4b0bf3
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08188079B2
Reaction notes
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