Triethylamine → Methyl {3'-[3-(2,4-dichlorophenyl)-2-propynyloxy]-4'-methoxybiphenyl-3-yl}acetate
Reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][C:16]([O:18][CH3:19])=[O:17])[CH:10]=2)=[CH:5][C:4]=1[O:20][CH2:21][C:22]#[CH:23].[Cl:24][C:25]1[CH:30]=[C:29]([Cl:31])[CH:28]=[CH:27][C:26]=1I.C(N(CC)CC)C>CN(C)C=O.C(OCC)(=O)C.[Cu](I)I>[Cl:24][C:25]1[CH:30]=[C:29]([Cl:31])[CH:28]=[CH:27][C:26]=1[C:23]#[C:22][CH2:21][O:20][C:4]1[CH:5]=[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][C:16]([O:18][CH3:19])=[O:17])[CH:10]=2)[CH:7]=[CH:8][C:3]=1[O:2][CH3:1]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Procedure
9 mg of methyl (4′-methoxy-3′-(2-propynyloxy)biphenyl-3-yl)acetate was dissolved in 0.1 ml of N,N-dimethylformamide, 30 mg of 2,4-dichloroiodobenzene, 2 mg of copper iodide, 2 mg of tetrakistriphenyl phosphine palladium and 0.05 ml of triethylamine were added thereto, and the mixture was stirred at room temperature for 3 days. The reaction mixture was diluted with ethyl acetate and washed with water. The organic layer was concentrated to give methyl {3′-[3-(2,4-dichlorophenyl)-2-propynyloxy]-4′-methoxybiphenyl-3-yl}acetate. This product was dissolved in 0.5 ml of ethanol, then 0.1 ml of 5N sodium hydroxide was added thereto, and the mixture was left overnight at room temperature. The reaction mixture was neutralized with 1N hydrochloric acid and extracted with ethyl acetate. The organic layer was concentrated, and the residue was purified by reverse-phase high performance liquid chromatography to give 4.24 mg of the title compound.
Workup
- washwashed with water
- concentrationThe organic layer was concentrated
Sources & evidence
- ORD record
- ord-650e5569671c45b3a81602ac9ff64696
- Source dataset
- uspto-grants-2010_03
- Patent number
- US07687664B2
Reaction notes
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