Pyridine → HCID 57460489, compound

HRID 1718586Notes

Reaction equation

HRID 1718586 reaction equation
[O:1]=[C:2]1[NH:7][CH:6]=[N:5][C:4]([CH2:8][CH2:9][CH3:10])=[C:3]1[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[C:19]([C:24]#[N:25])=[CH:20][CH:21]=[CH:22][CH:23]=2)=[CH:14][CH:13]=1.[CH3:26][C:27]1([CH3:39])[CH2:31][C:30]2[CH:32]=[C:33](B(O)O)[CH:34]=[CH:35][C:29]=2[O:28]1.C(N(CC)CC)C.N1C=CC=CC=1>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.C(OCC)(=O)C.C(Cl)Cl>[CH3:26][C:27]1([CH3:39])[CH2:31][C:30]2[CH:32]=[C:33]([N:7]3[C:2](=[O:1])[C:3]([CH2:11][C:12]4[CH:17]=[CH:16][C:15]([C:18]5[C:19]([C:24]#[N:25])=[CH:20][CH:21]=[CH:22][CH:23]=5)=[CH:14][CH:13]=4)=[C:4]([CH2:8][CH2:9][CH3:10])[N:5]=[CH:6]3)[CH:34]=[CH:35][C:29]=2[O:28]1

Participants

8

Reactant 4

HCID 1049PyridineHCID 8471TriethylamineHCID 23005350(2,2-Dimethyl-2,3-dihydro-1-benzofuran-5-yl)boronic acidHCID 135464158HCID 135464158, compound

Product 1

HCID 57460489HCID 57460489, compoundYield 54%

Reagents, catalysts & solvents 3

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4′-[(6-oxo-4-propyl-1,6-dihydropyrimidin-5-yl)methyl]biphenyl-2-carbonitrile (1.02 g), (2,2-dimethyl-2,3-dihydro-1-benzofuran-5-yl)boronic acid (0.78 g), molecular sieves 4 A (1.98 g), triethylamine (1.7 mL), pyridine (1.0 mL), copper(II) acetate (0.65 g) and methylene chloride (15 mL) was stirred at room temperature for 24 hr. Ethyl acetate was added to the reaction mixture, and the insoluble solid was filtered off. The solvent of the filtrate was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to give the title compound as a colorless solid (0.76 g, 54%).

Workup

  1. filtrationthe insoluble solid was filtered off
  2. customThe solvent of the filtrate was evaporated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ea7076312ad543d9b017fbcc873a44b4
Source dataset
uspto-grants-2010_09
Patent number
US07803940B2

Reaction notes

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