Pyridine → HCID 18694319, compound

HRID 751328Notes

Reaction equation

HRID 751328 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](=[O:10])[C:2]1=[O:11].[N:12]1[CH:17]=[CH:16][C:15](B(O)O)=[CH:14][CH:13]=1.C(N(CC)CC)C.N1C=CC=CC=1>ClCCl>[N:12]1[CH:17]=[CH:16][C:15]([N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[C:3](=[O:10])[C:2]2=[O:11])=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 7054IsatinHCID 8471TriethylamineHCID 2734379(Pyridin-4-yl)boronic acid

Product 1

HCID 18694319HCID 18694319, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1H-indole-2,3-dione (isatin, 552 mg, 3.75 mmol), pyridine-4-boronic acid (922 mg, 7.5 mmol), anhyd cupric acetate (1.36 mg, 7.5 mmol), activated 4A molecular sieve (2.0 g), triethylamine (1.05 mL, 7.5 mmol), pyridine (607 μL, 7.5 mmol) and dichloromethane (50 mL) is stirred for 24 hr at room temperature. The mixture is filtered through a pad of hyflo and evaporated. The residue is stirred with ethyl acetate, the insoluble copper salts removed by filtration and the filtrate is evaporated. The residue is purified by flash chromatography eluting with pentne-30 to 80% ethyl acetate to give the title compound.

Workup

  1. filtrationThe mixture is filtered through a pad of hyflo
  2. customevaporated
  3. stirringThe residue is stirred with ethyl acetate
  4. customthe insoluble copper salts removed by filtration
  5. customthe filtrate is evaporated
  6. customThe residue is purified by flash chromatography
  7. washeluting with pentne-30 to 80% ethyl acetate

Sources & evidence

ORD record
ord-3711081316ca490786a0a2112f13edb4
Source dataset
uspto-grants-2008_07
Patent number
US07405300B2

Reaction notes

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