Pyridine → HCID 18694319, compound

HRID 1678106Notes

Reaction equation

HRID 1678106 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 pentane-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 pentane-30 to 80% ethyl acetate

Sources & evidence

ORD record
ord-a2e863127fd545509e1a6b8162eddd76
Source dataset
uspto-grants-2011_08
Patent number
US08008491B2

Reaction notes

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