Water → HCID 22172845, compound
Reaction equation
Cl[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[C:9](=[O:11])[CH:8]([CH3:12])[CH2:7]2.[CH:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][C:14]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].O>C(O)CO.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:12][CH:8]1[CH2:7][C:6]2[C:10](=[C:2]([C:15]3[CH:14]=[CH:13][C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[CH:16]=3)[CH:3]=[CH:4][CH:5]=2)[C:9]1=[O:11]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 125 °C
Procedure
Using a method similar to Example 16 d), 2.16 g (0.012 mol) of (1), 2.27 g (0.0132 mol) of 2-naphthylboronic acid, 2.8 g (0.0264 mol) of sodium carbonate were placed in 40 ml of ethylene glycol/8 ml of water in the reaction vessel, the mixture was degassed a number of times and saturated with argon. After addition of 13.5 mg (0.06 mmol) of palladium acetate and 0.102 g (0.18 mmol) of TMSPP, the reaction mixture was stirred for 2 hours at 125° C. After addition of 40 ml of water, the aqueous phase was extracted 4 times with 50 ml each time of ether, the combined ether phases were washed with 50 ml of water and 50 ml of saturated sodium chloride solution and dried over magnesium sulfate. Removal of the solvent gave 3.0 g of (19) as an oil which tends to crystallize.
Workup
- customsimilar to Example 16 d
- customthe mixture was degassed a number of times
- extractionthe aqueous phase was extracted 4 times with 50 ml each time of ether
- washthe combined ether phases were washed with 50 ml of water and 50 ml of saturated sodium chloride solution
- dry with materialdried over magnesium sulfate
- customRemoval of the solvent
Sources & evidence
- ORD record
- ord-cd258878debb48d29b5bb10bbe787061
- Source dataset
- uspto-grants-2005_11
- Patent number
- US06963017B2
Reaction notes
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