Pyridine → HCID 22054277, compound

HRID 1830238Notes

Reaction equation

HRID 1830238 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH3:27])=[C:5]([C:18]([O:25][CH3:26])=[C:19]([O:23][CH3:24])[C:20]=1[O:21][CH3:22])[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([OH:17])=[C:11]([CH:16]=1)[C:12]([O:14][CH3:15])=[O:13].[CH3:28][O:29][C:30]1[CH:31]=[C:32](B(O)O)[CH:33]=[CH:34][CH:35]=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]([CH3:27])=[C:5]([C:18]([O:25][CH3:26])=[C:19]([O:23][CH3:24])[C:20]=1[O:21][CH3:22])[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:17][C:34]2[CH:33]=[CH:32][CH:31]=[C:30]([O:29][CH3:28])[CH:35]=2)=[C:11]([CH:16]=1)[C:12]([O:14][CH3:15])=[O:13]

Participants

7

Reactant 4

HCID 1049PyridineHCID 8471TriethylamineHCID 2734370(3-Methoxyphenyl)boronic acidHCID 21919163HCID 21919163, compound

Product 1

HCID 22054277HCID 22054277, compoundYield 19.3%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

Methyl 5-(3,4,5,6-tetramethoxy-2-methylbenzyl)-2-hydroxybenzoate (0.805 g, 2.14 mmol) was dissolved in methylene chloride (50 ml) and after adding thereto in sequence copper acetate (0.429 g, 2.36 mmol), 3-methoxyphenylboronic acid (0.651 g, 4.28 mmol), Molecular Sieves 4A (0.500 g), triethylamine (0.541 g, 5.35 mmol) and pyridine (0.423 g, 5.35 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 (hexand:ethyl acetate=4:1) to obtain the titled compound (0.200 g, 0.414 mmol, 19%).

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 (hexand:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-cb44a126ef6a4d38afc6a405a7a1c2df
Source dataset
uspto-grants-2006_06
Patent number
US07064124B2

Reaction notes

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