Ethanol → 4-(6-Cyano-5-methoxy-pyridin-2-yl)-benzoic acid ethyl ester
Reaction equation
Br[C:2]1[N:7]=[C:6]([C:8]#[N:9])[C:5]([O:10][CH3:11])=[CH:4][CH:3]=1.C([O-])([O-])=O.[Na+].[Na+].B(O)(O)[C:19]1[CH:24]=[CH:23][C:22]([C:25]([OH:27])=[O:26])=[CH:21][CH:20]=1.[CH2:30](O)[CH3:31]>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:30]([O:27][C:25](=[O:26])[C:22]1[CH:23]=[CH:24][C:19]([C:2]2[CH:3]=[CH:4][C:5]([O:10][CH3:11])=[C:6]([C:8]#[N:9])[N:7]=2)=[CH:20][CH:21]=1)[CH3:31]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 80 °C
Procedure
A solution of 6-bromo-3-methoxy-pyridine-2-carbonitrile from Example 13c in toluene is treated with 2 M Na2CO3 (aqueous), 4-carboxylphenylboronic acid (1 equiv.), ethanol and catalytic (Ph3P)4Pd) and is heated at 80° C. for 18 h. The reaction mixture is evaporated and the residue is dissolved in ethanol with 4 N HCl in dioxane and heated at reflux for 18 h. The reaction mixture is evaporated, the residue taken into ethyl acetate, washed with 5% Na2CO3 (aqueous), dried over MgSO4 and evaporated to give 4-(6-cyano-5-methoxy-pyridin-2-yl)-benzoic acid ethyl ester.
Workup
- customThe reaction mixture is evaporated
- dissolutionthe residue is dissolved in ethanol with 4 N HCl in dioxane
- temperatureheated
- temperatureat reflux for 18 h
- customThe reaction mixture is evaporated
- washwashed with 5% Na2CO3 (aqueous)
- dry with materialdried over MgSO4
- customevaporated
Sources & evidence
- ORD record
- ord-3df59f582e864af8874b5c75ebad279c
- Source dataset
- uspto-grants-2005_03
- Patent number
- US06864267B2
Reaction notes
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