Water → Acetic acid 3,5-dichloro-4'-(4-trifluoromethyl-piperidine-1-carbonyl)-biphenyl-4-ylmethyl Ester
Reaction equation
[Cl:1][C:2]1[CH:12]=[C:11](B2OC(C)(C)C(C)(C)O2)[CH:10]=[C:9]([Cl:22])[C:3]=1[CH2:4][O:5][C:6](=[O:8])[CH3:7].Br[C:24]1[CH:29]=[CH:28][C:27]([C:30]([N:32]2[CH2:37][CH2:36][CH:35]([C:38]([F:41])([F:40])[F:39])[CH2:34][CH2:33]2)=[O:31])=[CH:26][CH:25]=1.C(=O)([O-])[O-].[K+].[K+].O>C(COC)OC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CO>[Cl:22][C:9]1[CH:10]=[C:11]([C:24]2[CH:25]=[CH:26][C:27]([C:30]([N:32]3[CH2:37][CH2:36][CH:35]([C:38]([F:40])([F:39])[F:41])[CH2:34][CH2:33]3)=[O:31])=[CH:28][CH:29]=2)[CH:12]=[C:2]([Cl:1])[C:3]=1[CH2:4][O:5][C:6](=[O:8])[CH3:7]Participants
9
Reactant 4
Product 1
Reagents, catalysts & solvents 4
Conditions
- Temperature
- 80 °C
Procedure
Dissolve 18.5 g (1 eq.) of Acetic acid 2,6-dichloro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzyl ester and 19.9 g (1.1 eq.) of (4-Bromo-phenyl)-(4-trifluoromethyl-piperidin-1-yl)-methanone in 190 mL of dimethoxyethane. Add 8.9 g of potassium carbonate, 95 mL of water, 0.24 g (0.02 eq.) of palladium acetate and 0.85 g (0.06 eq.) of triphenylphosphine. Heat the mixture at 80° C. for 2.5 hours. Stir the reaction mixture at room temperature overnight to afford a suspension. Add 7.4 g of potassium carbonate, 100 mL of water and 100 mL of methanol and stir the mixture at room temperature for 3 hours. Collect the solid by filtration and dry in a vacuum oven at 50° C. to afford 20.8 g (82% yield) of the titled compound.
Workup
- customto afford a suspension
- stirringstir the mixture at room temperature for 3 hours
- customCollect the solid
- filtrationby filtration
- customdry in a vacuum oven at 50° C.
Sources & evidence
- ORD record
- ord-1147736152ca4270ac128776b5ee98a2
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08153807B2
Reaction notes
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