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With copper(l) iodide; 4-(4-(dihexadecylamino)styryl)-N-methylpyridinium iodide; tri-tert-butyl phosphine;bis(benzonitrile)palladium(II) dichloride; In 1,4-dioxane; hexane; at 20.0℃;
Methyl 3-bromobenzofuran-5-carboxylate (750 mg, 2.94 mmol) is combined with bis(benzonitrile)palladium dichloride (169 mg, 0.44 mmol), cuprous iodide (19 mg, 0.10 mmol), tri-t-butylphosphine ((10% in hexane) 1.92 ml, 0.95 mmol), and propyne (2 ml, 35 mmol) in 7 ml dry dioxane in 15 ml screw cap pressure tube under nitrogen. The mixture is treated with DIA (494 muL, 3.6 mmol), is stirred overnight at RT, and is diluted with 50 ml EtOAc. The reaction is washed with 4×25 ml 1:1:0.1 H2O/brine/conc. NH4OH, the organic layer is dried (MgSO4), and the volatiles are removed in vacuo. The crude material is chromatographed over 50 g silica gel (230-400 mesh) eluting with 12% EtOAc/hexane. The appropriate fractions are combined and concentrated to give 460 mg (73%) of methyl 3-prop-1-ynyl-1-benzofuran-5-carboxylate as a pale solid. MS for C13H10O3 (EI) m/z (rel. intensity): 214 (M)+.
1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0); zinc; In ISOPROPYLAMIDE; at 120.0℃; for 18h;
A mixture of ethyl and <strong>[501892-90-6]methyl 3-bromo-1-benzofuran-5-carboxylate</strong> (778 mg, 3.0 mmol) is combined with zinc cyanide (211 mg, 1.8 mmol), tris(dibenzylideneacetone)dipalladium (110 mg, 0.12 mmol), 1,1'-bis(diphenylphosphino)ferrocene (132 mg, 0.24 mmol) and zinc dust (46 mg, 0.72 mmol) in a dry flask under nitrogen. The vessel is purged with nitrogen, treated with dimethyl acetamide (6 mL) and heated to 120 C. for 18 h. The mixture is cooled to RT diluted with EtOAc (50 mL), filtered through celite and washed with 2N NH4OH (2×50 mL). The organics are further washed with NaCl (50 mL), dried (Na2SO4) and concentrated to a brown solid (763 mg). The crude material is chromatographed over 30 g slurry-packed silica gel, eluting with 12% EtOAc/hexane. The appropriate fractions are combined and concentrated to afford 280 mg (45%) of the mixed methyl and ethyl esters as a yellow solid (45% ethyl ester/55% methyl ester). The mixture of ethyl and methyl 3-cyano-1-benzofuran-5-carboxylate (270 mg, 1.3 mmol) is suspended in pH 7 buffer (11 mL), treated with a solution of pig liver esterase (64 mg) in pH 7 buffer (4 mL) and stirred vigorously at RT for 16 h. Acetone (2 mL) is added, the mixture is stirred for 24 h and filtered through celite. The filtrate is acidified to pH 2 with concentrated HCl. The resulting solid is stirred for 45 min, filtered and dried in a vacuum oven at 80 C. for 16 h to afford 100 mg (41%) of 3-cyano-1-benzofuran-5-carboxylic acid as a white solid. MS for C10H5NO3, (EI) m/z: 187 (M)+.
With copper(I) iodide; diisopropylamine;bis(benzonitrile)palladium(II) chloride; In 1,4-dioxane; hexane;
EXAMPLE 33 N-[(1S,2R,4R)-7-azabicyclo[2.2.1]hept-2-yl]-3-prop-1-ynyl-1-benzofuran-5-carboxamide fumarate <strong>[501892-90-6]Methyl-3-bromobenzofuran-5-carboxylate</strong> (750 mg, 2.94 mmol) is combined with bis(benzonitrile)palladium dichloride (169 mg, 0.44 mmol), cuprous iodide (19 mg, 0.10 mmol), tri-t-butylphosphine ((10% in hexane) 1.92 ml, 0.95 mmol), and propyne (2 ml, 35 mmol) in 7 ml dry dioxane in 15 ml screw cap pressure tube under nitrogen. The mixture is treated with diisopropylamine (494 muL, 3.6 mmol), is stirred overnight at RT, and is diluted with 50 ml EtOAc. The reaction is washed with 4*25 ml 1:1:0.1 H2O/brine/conc NH4OH, the organic layer is dried over MgSO4, and the volatiles are removed in vacuo. The crude material is chromatographed over 50 g silica gel (230-400 mesh) eluding with 12% EtOAc/hexane. The appropriate fractions are combined and concentrated to give 460 mg (73%) of methyl 3-prop-1-ynyl-1-benzofuran-5-carboxylate as a pale solid. MS (EI) m/z): 214 (M)+.
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