With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.564483-18-7,2-(Dicyclohexylphosphino)-2′,4′,6′-tri-i-propyl-1,1′-biphenyl,as a common compound, the synthetic route is as follows.
564483-18-7, Example 44A N-(2-Chloro-4-nitrophenyl)-1H-pyrrolo[2,3-b]pyridine-4-amine Variant A: A solution of 200 mg (1.31 mmol) of 4-chloro-1H-pyrrolo[2,3-b]pyridine, 271 mg (1.57 mmol) of 2-chloro-4-nitroaniline, 60 mg (0.07 mmol) of tris(dibenzylideneacetone)dipalladium, 62 mg (0.13 mmol) of dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine and 399 mg (2.88 mmol) of potassium carbonate in 2.00 ml of degassed tert-butanol is stirred in a sealed pressure vessel at 100 C. for 3 h. The mixture is then cooled to RT, and a further 136 mg (0.79 mmol) of 2-chloro-4-nitroaniline, 31 mg (0.07 mmol) of dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine and 30 mg (0.04 mmol of tris(dibenzylideneacetone)dipalladium are added and the mixture is stirred at 100 C. for a further 3 h. Variant B: A mixture of 200 mg (1.31 mmol) of 4-chloro-1H-pyrrolo[2,3-b]pyridine, 678 mg (3.93 mmol) of 2-chloro-4-nitroaniline, 60 mg (0.07 mmol) of tris(dibenzylideneacetone)dipalladium, 62 mg (0.13 mmol) of dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine and 399 mg (2.88 mmol) of potassium carbonate and 2.50 ml of degassed tert-butanol is stirred in a sealed pressure vessel at 100 C. for 3 h. After cooling to RT, the reaction mixtures of both synthesis variants are filtered through Celite, the Celite is washed with ethyl acetate and the filtrates are concentrated under reduced pressure. The residue is subjected to column chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 10:1 to 100% ethyl acetate). This gives 145 mg of the partially purified product (purity 67%), 30 mg of which are purified by preparative HPLC. LC-MS (Method 1): Rt=1.28 min. MS (ESI pos.): m/z=289 (M+H)+. 1H-NMR (DMSO-d6, 300 MHz): delta=6.14-6.23 (m, 1H), 6.90 (d, 1H), 7.15 (d, 1H), 7.31-7.40 (m, 1H), 8.08 (dd, 1H), 8.12 (d, 1H), 8.34 (d, 1H), 9.01 (s, 1H), 11.68 (s, 1H).
564483-18-7 2-(Dicyclohexylphosphino)-2′,4′,6′-tri-i-propyl-1,1′-biphenyl 11155794, achiral-phosphine-ligands compound, is more and more widely used in various fields.
Reference£º
Patent; Bayer HealthCare AG; US2008/269268; (2008); A1;,
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