With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.29949-84-6,Tris(3-methoxyphenyl)phosphine,as a common compound, the synthetic route is as follows.
EXAMPLE 81 7-(3-Methoxyphenyl)-1-(4-methylpiperazin-1-yl)naphthalene A mixture of 3-methoxy-1-bromobenzene (0.089 mL, 0.71 mmol), 7-trimethylstannyl-1-(4-methylpiperazin-1-yl)naphthalene (0.25 g, 0.64 mmol), bis(acetonitrile) palladium chloride (0.0085 g, 0.032 mmol), tri(3-methoxyphenyl)phosphine (0.023 g, 0.064 mmol), and butylated hydroxytoluene (BHT, about 0.001 g, antioxidant) in dimethyl formamide (12 mL) was warned to 110 C. for 2 hours. The reaction was cooled to room temperature and diluted with 1N aqueous lithium chloride (25 mL) and 1 N sodium hydroxide (2 mL); then extracted with ether (3X). The combined ether layer was washed with 1N aqueous lithium chloride and brine. The organic phase was dried over calcium sulfate and concentrated. The residue was purified by flash chromatography on silica gel (1*2.5 inches). Elution proceeded as follows: 75% ethyl acetate/hexane, 200 mL, nil; 2% methanol/ethyl acetate 200 mL and 10% methanol/ethyl acetate, 200 mL, 0.084 g of an oil. This oil was further purified by kugelrohr distillation (1 mm Hg). The distillation proceeded as follows: 110-130 C., 0.014 g of a mixture of the title product and 7-methyl-1-(4-methylpiperazin-1-yl)naphthalene: 200-220 C., 0.062 g (23%) of the title compound as a yellow oil: 1 H NMR delta 8.43 (incompletely resolved dd, J=1.2Hz, 1 h), 7.90 (d, J=9 Hz, 1 H), 7.74 (dd, J=2, 8.5 Hz, 1 H), 7.58 (d, J=8 Hz, 1 H), 7.43 (sym m, 2 H), 7.34 (dt, J=1.5, 7.5 Hz, 1 H), 7.29 (5, J=2 Hz, 1 H), 7.14 (dd, J=1, 7.5 Hz, 1 H), 6.96 (ddd, J=1,2.5, 8 Hz, 1H), 3.92 (s, 3 H) 3.20 (br s, 4 H), 2.75 (br s, 4 H), 2.44 (s, 3 H). The product was dissolved in chloroform and HCl gas was bubbled through the solution to form the hydrochloride salt. Concentration of this solution to about 1 mL. at the boil and addition of about 1 mL of ether caused the white crystalline product to precipitate. The hydrochloride salt weighted 0.057 g: mp 236-238 C. Analysis calculated for C22 H24 N2 O*HCl: C, 71.63; H, 6.83; N, 7.59. Found: C, 71.31; H, 6.92; N, 7.59.
29949-84-6, 29949-84-6 Tris(3-methoxyphenyl)phosphine 141534, achiral-phosphine-ligands compound, is more and more widely used in various fields.
Reference£º
Patent; Pfizer Inc.; US5597826; (1997); A;,
Phosphine ligand
Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate