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A chiral imidazolium-containing pyridine amide compound and its preparation method and application

A technology of imidazole pyridine amide and compound, applied in the field of asymmetric hydroboration reaction, can solve problems such as unreported, difficult P ligands and the like

Active Publication Date: 2020-03-10
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, iron or cobalt-catalyzed asymmetric hydroboration of styrenic substrates has not been reported so far, and the relatively difficult-to-synthesize P ligands have been used to catalyze styrenic substrates with cheap metal copper.

Method used

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  • A chiral imidazolium-containing pyridine amide compound and its preparation method and application
  • A chiral imidazolium-containing pyridine amide compound and its preparation method and application
  • A chiral imidazolium-containing pyridine amide compound and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0063] Example: The formula (2) is commercially available, and the halide formula (3) is prepared according to the literature (Tetrahedron: Asymmetry, 2016, 27, 163-170).

[0064] Preparation of compound formula (1)

example A1

[0065] Example A1: Preparation of Compound A1

[0066]

[0067] Under nitrogen protection, (S)-(1-phenyl-2-(2-iodophenyl)-4-benzyl-4,5-dihydro)-1H-imidazole (0.4438g, 1.01mmol, 1.0equiv) With 2-pyridinecarboxamide (0.1461g, 1.20mmol, 1.2equiv) in 5.0mL dioxane, CuI (0.0191g, 0.1mmol, 10mol%), ethylenediamine (0.0120g, 0.2mmol, 20mol%) , Potassium phosphate trihydrate (0.5326g, 2.0mmol, 2.0equiv), reacted at 60°C for 48 hours, petroleum ether: ethyl acetate = 3:1 through the column, to obtain 0.2509g (0.58mmol, yield 58%) containing imidazopyridine Amide compound A1.

[0068] 1 H NMR(400MHz, CDCl 3 )δ12.79(s,1H), 8.80(d,J=8.4Hz,1H), 8.59(d,J=4.8Hz,1H), 8.31(d,J=8.0Hz,1H), 7.89(td, J=7.6,1.6Hz,1H),7.48-7.34(m,2H),7.36-7.25(m,4H),7.23-7.18(m,1H),7.16-7.02(m,3H),6.97-6.86( m, 2H), 6.68 (d, J = 8.4 Hz 2H), 4.75-4.65 (m, 1H), 4.14 (dd, J = 10.4, 9.6 Hz, 1H), 3.65-3.50 (m, 2H), 2.90 ( dd,J=14.0,9.2Hz,1H); 13 C NMR(101MHz, CDCl 3 )δ163.1, 159.8, 150.6, 148.1, 142.7, 138.5, 137.7, 137.3...

example A2

[0069] Example A2: Preparation of Compound A2

[0070]

[0071] Under nitrogen protection, (S)-(1-phenyl-2-(2-iodophenyl)-4-phenyl-4,5-dihydro)-1H-imidazole (0.4243g, 1.00mmol, 1.0equiv) With 6-methyl-2-pyridinecarboxamide (0.1634g, 1.20mmol, 1.2equiv) in 5.0mL dioxane, CuI (0.0381g, 0.2mmol, 20mol%), ethylenediamine (0.0120g, 0.2 mmol, 20mol%), potassium phosphate (0.4246g, 2.0mmol, 2.0equiv), reacted at 100°C for 24 hours, petroleum ether: ethyl acetate = 3:1 through the column to obtain 0.2361g (0.53mmol, 53%) containing imidazole Compound A2 of pyridine amide.

[0072] 1 H NMR(400MHz, CDCl 3 )δ12.84(s,1H), 8.75(d,J=8.4Hz,1H), 8.06(d,J=7.6Hz,1H), 7.72(t,J=7.6Hz,1H),7.45-7.37( m,3H),7.30-7.16(m,5H),7.13(t,J=8.0Hz,2H),6.99-6.80(m,2H),6.80(dd,J=8.4,1.0Hz,2H),5.59 (dd, J = 10.4, 8.8 Hz, 1H), 4.44 (dd, J = 10.8, 9.6 Hz, 1H), 3.94 (dd, J = 9.2, 8.8 Hz, 1H), 2.21 (s, 3H). 13 C NMR(101MHz, CDCl 3 )δ163.5,160.8,157.3,149.8,143.6,142.8,138.0,137.3,130.9,130.2,128.8,128.5,127.3,126.8,12...

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Abstract

The invention discloses a compound containing chiral imidazole picolinamide. The compound is shown as a formula (I). The invention further discloses a preparation method and application of the compound containing chiral imidazole picolinamide. The compound containing chiral imidazole picolinamide provided by the invention can serve as a catalyst, and is used for preparing a chiral organoboron compound by performing asymmetric hydroboration addition on carbon-carbon atomic double bonds of a prochiral organic compound. The ee value is 99%. The structural formula is as shown in the specification.

Description

Technical field [0001] The invention relates to the synthesis of a compound containing chiral imidazole pyridine amides and a preparation method thereof, as well as the use of the compound and cobalt to co-catalyze the asymmetric hydroboration reaction of olefins. Background technique [0002] Organoboron ester compounds are a very important class of organic synthetic building blocks, which can selectively construct different chemical bonds (CC, CO, CN, CX, etc.) [D. Leonori,; VKAggarwal, Angew.Chem., Int.Ed .2015,54,1082.]. In drug development, boric acid is often used as a key synthetic intermediate, and it can also replace the carboxyl group of carboxylic acid drugs to improve the efficacy, which is of great significance for new drug development. In recent years, many stereospecific conversion methods of chiral boron esters have been developed [C.Sandford,VKAggarwal,Chem.Commun.2017,53,5481.], so as to obtain a series of other chiral molecules with different functional groups...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/12B01J31/22C07F5/02C07B53/00
CPCB01J31/1815B01J2531/0244B01J2531/845C07B53/00C07B2200/07C07D401/12C07F5/025
Inventor 陆展陈旭程朝阳
Owner ZHEJIANG UNIV
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