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Preparation method of [(S)-(-)-2, 2'-bis (diphenylphosphine)-1, 1'-binaphthalene] palladium dichloride

A technology of diphenylphosphine and palladium dichloride, which is applied in the field of preparation of pharmaceutical intermediates, can solve the problems of low reaction yield, large metal consumption, and low product purity, and achieve high reaction yield and high metal utilization rate , Good product quality effect

Pending Publication Date: 2021-01-08
XIAN CATALYST NEW MATERIALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The current process is to directly cooperate with the ligand corresponding to the compound and the metal compound to react, such a reaction yield is low, the metal unit consumption is large, and the purity of the obtained product is relatively low

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] A preparation method of [(S)-(-)-2,2'-bis(diphenylphosphine)-1,1'-binaphthyl]palladium dichloride, comprising the following steps:

[0018] (1) Under nitrogen protection, 11.45g (S)-(-)-2,2'-bis(diphenylphosphine)-1,1'-binaphthalene was mixed with 35mL dichloromethane (AR) at 30°C Dissolve under stirring to obtain an organic solution of (S)-(-)-2,2'-bis(diphenylphosphine)-1,1'-binaphthalene;

[0019] (2) Dissolve 5.0g (1,5-cyclooctadiene)palladium(II) dichloride in 15mL of dichloromethane (AR), and then add dropwise to the (S)-(-)-2,2 In the organic solution of '-bis(diphenylphosphine)-1,1'-binaphthalene, stir the reaction at 30°C for 5h, then heat and concentrate at 30°C until the solid precipitates, filter, and wash with 3 times the volume of water After filtering again, the obtained filter cake was vacuum-dried at 30°C and -0.08MPa for 10 hours to obtain [(S)-(-)-2,2'-bis(diphenylphosphine)-1,1'-bis Naphthalene] palladium dichloride 13.82g;

[0020] In this exampl...

Embodiment 2

[0022] A preparation method of [(S)-(-)-2,2'-bis(diphenylphosphine)-1,1'-binaphthyl]palladium dichloride, comprising the following steps:

[0023] (1) Under nitrogen protection, 9.8g (S)-(-)-2,2'-bis(diphenylphosphine)-1,1'-binaphthalene was mixed with 29.4mL toluene (AR) at 50°C Stir and dissolve to obtain an organic solution of (S)-(-)-2,2'-bis(diphenylphosphine)-1,1'-binaphthalene;

[0024] (2) Dissolve 5.0g (2,2`-bipyridyl)palladium(II) dichloride in 15mL of toluene (AR), then add dropwise to the (S)-(-)-2,2'-bis In the organic solution of (diphenylphosphine)-1,1'-binaphthalene, stir and react at 80°C for 10h, then heat and concentrate at 30°C until solid precipitates, filter, wash with 3 times the volume of water and filter again , the obtained filter cake was vacuum-dried at 60°C and -0.095MPa for 3h to obtain [(S)-(-)-2,2'-bis(diphenylphosphine)-1,1'-binaphthyl]bis Palladium chloride 11.77g;

[0025] In this example, the molar yield of the product [(S)-(-)-2,2'-bis(d...

Embodiment 3

[0027] A preparation method of [(S)-(-)-2,2'-bis(diphenylphosphine)-1,1'-binaphthyl]palladium dichloride, comprising the following steps:

[0028] (1) Under nitrogen protection, stir 4.66g (S)-(-)-2,2'-bis(diphenylphosphine)-1,1'-binaphthyl with 14mL tetrahydrofuran (AR) at 50°C Dissolving to obtain an organic solution of (S)-(-)-2,2'-bis(diphenylphosphine)-1,1'-binaphthyl;

[0029] (2) Dissolve 5.0 g of bis(triphenylphosphine)palladium(II) dichloride in 15 mL of tetrahydrofuran (AR), and then add dropwise to the (S)-(-)-2,2'-bis(di In the organic solution of phenylphosphine)-1,1'-binaphthalene, stir the reaction at 50°C for 8h, then heat and concentrate at 50°C until the solid precipitates, filter, wash with 3 times the volume of water, and then filter again. The obtained filter cake was vacuum dried at 30°C and -0.095MPa for 8 hours to obtain [(S)-(-)-2,2'-bis(diphenylphosphine)-1,1'-binaphthyl]dichloride Palladium 5.6g;

[0030] In this example, the molar yield of the pr...

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PUM

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Abstract

The invention discloses a preparation method of [(S)-(-)-2, 2'-bis (diphenylphosphine)-1, 1'-binaphthalene] palladium dichloride, which comprises the following steps: (1) under the protection of nitrogen, dissolving (S)-(-)-2, 2 '-bis (diphenylphosphine)-1, 1'-binaphthalene by stirring with an organic solvent at 30-50 DEG C; and (2) dissolving a complex of divalent palladium by using an organic solvent, dropwise adding into the solution obtained in the step (1), stirring and reacting for 5-10h at the temperature of 30-80 DEG C, heating and concentrating until a solid is separated out, filtering, washing with water, filtering again, and carrying out vacuum drying on an obtained filter cake. According to the preparation method, a divalent palladium complex is directly used as a metal precursor, [(S) (2, 2 '-bis (diphenylphosphine) 1, 1' binaphthalene] is used as a ligand, the reaction process is simple, and the reaction yield is high.

Description

technical field [0001] The invention belongs to the technical field of preparation of pharmaceutical intermediates, in particular to the preparation of [(S)-(-)-2,2'-bis(diphenylphosphine)-1,1'-binaphthyl]palladium dichloride method. Background technique [0002] The synthesis of chiral compounds is the foreword science of chemical synthesis at present. Chiral compounds are widely used in medicine, liquid crystal materials, functional materials, fine chemicals, etc. Fast, high yield, high selectivity and other advantages, it has great advantages in chiral synthesis. [0003] [(S)-(-)-2,2'-bis(diphenylphosphine)-1,1'-binaphthyl]palladium dichloride in specific asymmetric hydrogenation, Heck, Suzuki reaction and other organic synthesis reactions Precious metal catalysts that play an important role. [0004] The current technology uses the ligand corresponding to the compound to react directly with the metal compound. Such a reaction has low yield, high metal consumption, an...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00
CPCC07F15/0066
Inventor 姚琪谢权韩彬张高鹏校大伟李小安潘丽娟高武
Owner XIAN CATALYST NEW MATERIALS CO LTD