Pyridine → HCID 57460767, compound

HRID 1674154Notes

Reaction equation

HRID 1674154 reaction equation
[CH2:1]([O:3][C:4]1[N:5]=[C:6]([CH3:26])[NH:7][C:8](=[O:25])[C:9]=1[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[C:18]([C:23]#[N:24])=[CH:19][CH:20]=[CH:21][CH:22]=2)=[CH:13][CH:12]=1)[CH3:2].[O:27]1[C:31]2[CH:32]=[CH:33][C:34](B(O)O)=[CH:35][C:30]=2[CH2:29][CH2:28]1.C(N(CC)CC)C.N1C=CC=CC=1>O1CCCC1.C(OCC)(=O)C.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[O:27]1[C:31]2[CH:32]=[CH:33][C:34]([N:7]3[C:8](=[O:25])[C:9]([CH2:10][C:11]4[CH:16]=[CH:15][C:14]([C:17]5[C:18]([C:23]#[N:24])=[CH:19][CH:20]=[CH:21][CH:22]=5)=[CH:13][CH:12]=4)=[C:4]([O:3][CH2:1][CH3:2])[N:5]=[C:6]3[CH3:26])=[CH:35][C:30]=2[CH2:29][CH2:28]1

Participants

8

Reactant 4

HCID 1049PyridineHCID 8471TriethylamineHCID 2773380(2,3-Dihydro-1-benzofuran-5-yl)boronic acidHCID 57460766HCID 57460766, compound

Product 1

HCID 57460767HCID 57460767, compoundYield 92%

Reagents, catalysts & solvents 3

HCID 8895Cupric acetateCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 4′-[(4-ethoxy-2-methyl-6-oxo-1,6-dihydropyrimidin-5-yl)methyl]biphenyl-2-carbonitrile (0.17 g), 2,3-dihydro-1-benzofuran-5-ylboronic acid (0.16 g), triethylamine (0.17 mL), pyridine (0.34 mL) and molecular sieves 4 A (0.34 g) in tetrahydrofuran (5 mL) was added copper(II) acetate (0.17 g), and the mixture was stirred for 1 day. The reaction mixture was diluted with ethyl acetate, the insoluble material was filtered off through celite, and the filtrate was concentrated. The residue was purified by silica gel column chromatography to give the title compound as a colorless solid (0.21 g, 92%).

Workup

  1. filtrationthe insoluble material was filtered off through celite
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-0d253a6ea0f94e819cb90ecce5e2d73e
Source dataset
uspto-grants-2011_08
Patent number
US07998968B2

Reaction notes

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