Triethylamine → HCID 58525563, compound

HRID 1894967Notes

Reaction equation

HRID 1894967 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12]([O:14][CH3:15])=[O:13])=[CH:5]2.C(N(CC)CC)C.[C:23]1(B(O)O)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(Cl)Cl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[O:1]([C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12]([O:14][CH3:15])=[O:13])=[CH:5]2)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 66827Phenylboronic AcidHCID 58525572HCID 58525572, compound

Product 1

HCID 58525563HCID 58525563, compound

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of methyl 6-hydroxyquinoline-3-carboxylate (0.142 g, 0.699 mmol) in methylene chloride (7 mL) and triethylamine (0.974 mL, 6.99 mmol) were added phenylboronic acid (197 mg, 1.62 mmol), copper(II) acetate (294 mg, 1.62 mmol) and 4 Å molecular sieves (approx 200 mg). The mixture was stirred at room temperature over night. Solids were removed from the reaction mixture by filtration and the filter pad was washed thoroughly with ethyl acetate. The filtrate was washed twice with ammonium hydroxide solution and then brine. The extracts were dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude residue was purified by silica gel chromatography (hexanes to 50/50 hexanes/ethyl acetate gradient) to afford Int-17 (0.143 g, 73%). LC-MS: (FA) ES+280; 1H NMR (400 MHz, d6-DMSO) δ ppm 9.22 (d, J=2.1 Hz, 1H), 8.95 (d, J=1.8 Hz, 1H), 8.13 (d, J=8.8 Hz, 1H), 7.70-7.66 (m, 2H), 7.49-7.43 (m, 2H), 7.23 (tt, J=7.5, 7.5, 1.1, 1.1 Hz, 1H), 7.17-7.13 (m, 2H), 3.93 (s, 3H).

Workup

  1. customSolids were removed from the reaction mixture by filtration
  2. washthe filter pad was washed thoroughly with ethyl acetate
  3. washThe filtrate was washed twice with ammonium hydroxide solution
  4. dry with materialThe extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude residue was purified by silica gel chromatography (hexanes to 50/50 hexanes/ethyl acetate gradient)
  8. customto afford Int-17 (0.143 g, 73%)

Sources & evidence

ORD record
ord-32d33f93ecb5448c9f39785992dabfbc
Source dataset
uspto-grants-2013_08
Patent number
US08513421B2

Reaction notes

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