Pyridine → HCID 19876397, compound

HRID 751327Notes

Reaction equation

HRID 751327 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[O:12].[C:13]1(B(O)O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC)CC)C.N1C=CC=CC=1>ClCCl>[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:6](=[O:11])[C:5]2=[O:12]

Participants

6

Reactant 4

HCID 1049PyridineHCID 8471TriethylamineHCID 118405-MethylisatinHCID 66827Phenylboronic Acid

Product 1

HCID 19876397HCID 19876397, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 5-methyl-1H-indole-2,3-dione (5-methylisatin, 2.0 g, 12.41 mmol), phenylboronic acid (3.027 g, 24.82 mmol), anhyd cupric acetate (4.50 g, 24.77 mmol), activated 4A molecular sieve (6.6 g), triethylamine (3.47 mL, 24.9 mmol), pyridine (2.01 mL, 24.9 mmol) and dichloromethane (165 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 dichloromethane to give the title compound (1.91 g, 65% yield) as an orange solid. MS 238 (M+H).

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 dichloromethane

Sources & evidence

ORD record
ord-05b57829b19144f8a020d93f2e46c31f
Source dataset
uspto-grants-2008_07
Patent number
US07405300B2

Reaction notes

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