Pyridine → HCID 57460476, compound

HRID 1673902Notes

Reaction equation

HRID 1673902 reaction equation
[CH2:1]([C:3]1[N:4]=[C:5]([CH3:25])[NH:6][C:7](=[O:24])[C:8]=1[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[C:17]([C:22]#[N:23])=[CH:18][CH:19]=[CH:20][CH:21]=2)=[CH:12][CH:11]=1)[CH3:2].[CH3:26][CH:27]1[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>[CH2:1]([C:3]1[N:4]=[C:5]([CH3:25])[N:6]([C:33]2[CH:34]=[CH:35][C:29]3[O:28][CH:27]([CH3:26])[CH2:31][C:30]=3[CH:32]=2)[C:7](=[O:24])[C:8]=1[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[C:17]([C:22]#[N:23])=[CH:18][CH:19]=[CH:20][CH:21]=2)=[CH:12][CH:11]=1)[CH3:2]

Participants

8

Reactant 4

HCID 1049PyridineHCID 8471TriethylamineHCID 43297227(2-Methyl-2,3-dihydro-1-benzofuran-5-yl)boronic acidHCID 135428141HCID 135428141, compound

Product 1

HCID 57460476HCID 57460476, compoundYield 78%

Reagents, catalysts & solvents 3

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4′-[(4-ethyl-2-methyl-6-oxo-1,6-dihydropyrimidin-5-yl)methyl]biphenyl-2-carbonitrile (0.99 g), (2-methyl-2,3-dihydro-1-benzofuran-5-yl)boronic acid (0.98 g), molecular sieves 4 A (0.49 g), triethylamine (2.1 mL), pyridine (1.0 mL), copper(II) acetate (1.09 g) and methylene chloride (20 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 colorless crystals (1.08 g, 78%).

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-8dfeeff51e694785a5bafbe05919f146
Source dataset
uspto-grants-2011_08
Patent number
US07998968B2

Reaction notes

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