Pyridine → HCID 19876397, compound

HRID 1678105Notes

Reaction equation

HRID 1678105 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-2254aa805f9743ba9b2f71650b15a782
Source dataset
uspto-grants-2011_08
Patent number
US08008491B2

Reaction notes

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