3-(Tetramethyl-1,3,2-dioxaborolan-2-yl)-5-(trifluoromethyl)pyridine → 4,6-Dimethyl-5'-trifluoromethyl-[2,3']bipyridinyl-5-carboxylic acid ethyl ester
Reaction equation
[CH2:1]([O:3][C:4](=[O:14])[C:5]1[C:10]([CH3:11])=[CH:9][C:8](Cl)=[N:7][C:6]=1[CH3:13])[CH3:2].CC1(C)C(C)(C)OB([C:23]2[CH:24]=[N:25][CH:26]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:28]=2)O1>>[CH2:1]([O:3][C:4]([C:5]1[C:10]([CH3:11])=[CH:9][C:8]([C:23]2[CH:24]=[N:25][CH:26]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:28]=2)=[N:7][C:6]=1[CH3:13])=[O:14])[CH3:2]Participants
Procedure
In analogy to the procedures described for example 1, for intermediate 5B and for intermediate 1, the title compound has been prepared by the following reaction sequence: i) 6-chloro-2,4-dimethyl-nicotinic acid ethyl ester [Zhou, Y.; Bridger, G. J.; Skerlj, R. T.; Bogucki, D.; Yang, W.; Bourque, E.; Langille, J.; Li, T.-S.; Metz, M. U.S. Pat. Appl. Publ. (2005), US 2005277668 A1] was reacted with 3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-5-trifluoromethyl-pyridine (intermediate 6) to give 4,6-dimethyl-5′-trifluoromethyl-[2,3′]bipyridinyl-5-carboxylic acid ethyl ester; ii) 4,6-dimethyl-5′-trifluoromethyl-[2,3′]bipyridinyl-5-carboxylic acid ethyl ester has been saponified to give 4,6-dimethyl-5′-trifluoromethyl-[2,3′]bipyridinyl-5-carboxylic acid; iii) 4,6-dimethyl-5′-trifluoromethyl-[2,3′]bipyridinyl-5-carboxylic acid was converted into its acid chloride and reacted with 4-pyrrolidin-1-yl-piperidine to give the title compound as colorless amorphous solid. MS: 433.3 (MH+).
Sources & evidence
- ORD record
- ord-fc9e049cff794a2990acb8ddc65e4a67
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08153805B2
Reaction notes
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