Pyridine → HCID 22054173, compound

HRID 1830255Notes

Reaction equation

HRID 1830255 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH3:31])=[C:5]([C:22]([O:29][CH3:30])=[C:23]([O:27][CH3:28])[C:24]=1[O:25][CH3:26])[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([OH:21])=[C:11]([CH:20]=1)[C:12]([N:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1)=[O:13].[N:32]1[CH:37]=[CH:36][CH:35]=[C:34](B(O)O)[CH:33]=1.C(N(CC)CC)C.N1C=CC=CC=1>C(Cl)Cl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:1][O:2][C:3]1[C:4]([CH3:31])=[C:5]([C:22]([O:29][CH3:30])=[C:23]([O:27][CH3:28])[C:24]=1[O:25][CH3:26])[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:21][C:34]2[CH:33]=[N:32][CH:37]=[CH:36][CH:35]=2)=[C:11]([CH:20]=1)[C:12]([N:14]1[CH2:15][CH2:16][O:17][CH2:18][CH2:19]1)=[O:13]

Participants

7

Reactant 4

HCID 1049PyridineHCID 8471TriethylamineHCID 27343783-Pyridinylboronic acidHCID 22054155HCID 22054155, compound

Product 1

HCID 22054173HCID 22054173, compoundYield 42.4%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

N-[5-(3,4,5,6-Tetramethoxy-2-methylbenzyl)-2-hydroxybenzoyl]morpholine (0.100 g, 0.232 mmol) was dissolved in methylene chloride (2.5 ml) and after adding thereto in sequence copper acetate (0.042 g, 0.232 mmol), 3-pyridylboronic acid (0.076 g, 0.464 mmol), Molecular Sieves 4A (0.100 g), triethylamine (0.059 g, 0.580 mmol) and pyridine (0.046 g, 0.580 mmol), the solution was stirred at room temperature for 12 hours. The reaction solution was filtered and the filtrate was poured into water and then extracted with methylene chloride. The extract was washed with saturated brine, then dried and concentrated. The obtained residue was purified by silica gel column chromatography (chloroform:methanol=9:1) to obtain the titled compound (0.050 g, 0.0984 mmol, 42%).

Workup

  1. additionafter adding
  2. filtrationThe reaction solution was filtered
  3. additionthe filtrate was poured into water
  4. extractionextracted with methylene chloride
  5. washThe extract was washed with saturated brine
  6. customdried
  7. concentrationconcentrated
  8. customThe obtained residue was purified by silica gel column chromatography (chloroform:methanol=9:1)

Sources & evidence

ORD record
ord-37090973983841c1b2c3ac35f652dc5d
Source dataset
uspto-grants-2006_06
Patent number
US07064124B2

Reaction notes

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