Potassium Phosphate, Tribasic → Methyl 2-chloro-5-methylnicotinate
Reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]([Cl:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[O-]P([O-])([O-])=O.[K+].[K+].[K+].[CH3:21]B(O)O.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>C1(C)C=CC=CC=1.O.CC([O-])=O.CC([O-])=O.[Pd+2]>[Cl:12][C:5]1[N:4]=[CH:3][C:2]([CH3:21])=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 100 °C
Procedure
To a solution of methyl 5-bromo-2-chloronicotinate (1.05 g, 4.19 mmol), K3PO4 (2.95 g, 13.90 mmol), methylboronic acid (0.32 g, 5.26 mmol) and tricyclohexylphosphine (0.11 g, 0.39 mmol) in toluene/water (16 ml/0.8 ml) under nitrogen atmosphere was added Pd(OAc)2 (0.04 g, 0.18 mmol). The mixture was heated at 100° C. overnight under nitrogen atmosphere. The reaction mixture was then cooled to room temperature and concentrated in vacuum. Ethyl acetate was added to the residue and this organic layer was washed with water, brine, dried over MgSO4, filtered and the solvent evaporated under vacuum to yield the desired product as a yellow oil. Yield=87%
Workup
- temperatureThe reaction mixture was then cooled to room temperature
- concentrationconcentrated in vacuum
- additionEthyl acetate was added to the residue
- washthis organic layer was washed with water, brine
- dry with materialdried over MgSO4
- filtrationfiltered
- customthe solvent evaporated under vacuum
Sources & evidence
- ORD record
- ord-fed20cce1bcf4d6db64c93351143fcf6
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08258308B2
Reaction notes
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