Triethylamine → HCID 86600202, compound
Reaction equation
[CH:1]([O:4][C:5](=[O:14])[C:6]1[CH:11]=[C:10](Br)[CH:9]=[C:8](Br)[CH:7]=1)([CH3:3])[CH3:2].C(N([CH2:20][CH3:21])CC)C.C[Si:23]([C:26]#C)([CH3:25])[CH3:24].C(OCC)(=O)C>CCCCCC.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH:1]([O:4][C:5](=[O:14])[C:6]1[CH:11]=[C:10]([Si:23]([CH3:26])([CH3:25])[CH3:24])[CH:9]=[C:8]([Si:23]([CH3:26])([CH3:25])[CH3:24])[C:7]=1[C:20]#[CH:21])([CH3:3])[CH3:2]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Procedure
Following General Procedure D and using 3,5-dibromo-benzoic acid isopropyl ester (Intermediate 205, 2.7 g, 8.6 mmol), triethyl amine (30 mL), copper(I)iodide (0.45 g, 2.4 mmol), trimethylsilyl acetylene (6.8 mL, 48 mmol) and dichlorobis(triphenylphosphine)palladium(II) (1.75 g, 2.4 mmol) followed by flash column chromatography over silica gel (230-400 mesh) using 3% ethyl acetate in hexane as the eluent, the intermediate 3,5-bis-trimethylsilanylethynyl-benzoic acid isopropyl ester was obtained. The intermediate (2.8 g, 7.85 mmol) was treated with a 1M solution of tetra-n-butyl ammonium fluoride in tetrahydrofuran (25 mL, 25 mmol) and the resulting reaction mixture was stirred in an ice bath for 1 h. Water was added and the reaction mixture was extracted with diethyl ether. The organic phase was washed with water and brine, dried over anhydrous sodium sulfate, filtered and evaporated to an oil that was redissolved in diethyl ether (10 mL) and treated with hexane (150 mL). The solid that precipitated out was filtered and dried to afford the title compound (1.3 g, 78%).
Sources & evidence
- ORD record
- ord-70ab3f2bdd654b69977c7fc566618c6f
- Source dataset
- uspto-grants-2009_12
- Patent number
- US07638648B2
Reaction notes
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