Potassium Carbonate → HCID 21868347, compound

HRID 551524Notes

Reaction equation

HRID 551524 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([CH2:12][CH2:13][OH:14])[CH:6]=[CH:5]2.[N:15]1[NH:16][C:17](=[O:21])[CH:18]=[CH:19][CH:20]=1.C([O-])([O-])=O.[K+].[K+]>N1C=CC=CC=1.[Cu]>[OH:14][CH2:13][CH2:12][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[CH:3]=[C:2]([N:16]1[C:17](=[O:21])[CH:18]=[CH:19][CH:20]=[N:15]1)[CH:11]=[CH:10]2

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 681533(2H)-PyridazinoneHCID 251961662-(6-Bromonaphthalen-2-yl)ethan-1-ol

Product 1

HCID 21868347HCID 21868347, compoundYield 54.2%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 1049PyridineSolvent

Procedure

A mixture of the product from Example 31E (500 mg, 1.87 mmol), 2H-pyridazin-3-one (180 mg, 1.87 mmol), copper powder (120 mg, 1.87 mmol), and K2CO3 (775 mg, 5.61 mmol, 3 equiv.) in pyridine (75 mL) was stirred at reflux under a dry nitrogen atmosphere for 20 hr. The reaction mixture was cooled to room temperature then concentrated under reduced pressure. Residual pyridine was removed by repeated evaporation with toluene. The residue was partitioned between ethyl acetate (350 mL) and saturated aqueous Na2CO3. The organic layer was washed twice with aqueous NH4OH, dried (MgSO4), filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (75:25 ethyl acetate/hexane) to provide the title compound (270 mg, 54% yield). 1H NMR (CDCl3, 300 MHz) δ 8.11 (d, J=2 Hz, 1H), 7.97-7.93 (m, 1H), 7.88 (t, J=9 Hz, 2H), 7.75-7.68 (m, 2H), 7.41 (dd, J=2, 12 Hz, 1H), 7.31-7.24 (m, 1H), 7.10 (dd, J=2, 12 Hz, 1H), 3.97 (t, J=6 Hz, 2H), 3.06 (t, J=6 Hz, 2H). MS (DCl-NH3) [M+H]+ at 267, [M+NH4]+ at 284.

Workup

  1. temperatureat reflux under a dry nitrogen atmosphere for 20 hr
  2. concentrationthen concentrated under reduced pressure
  3. customResidual pyridine was removed
  4. customevaporation with toluene
  5. customThe residue was partitioned between ethyl acetate (350 mL) and saturated aqueous Na2CO3
  6. washThe organic layer was washed twice with aqueous NH4OH
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationthe filtrate was concentrated under reduced pressure
  10. customThe residue was purified by column chromatography (75:25 ethyl acetate/hexane)

Sources & evidence

ORD record
ord-c6e3fde119034730b5a7ebd4dac2cbc7
Source dataset
uspto-grants-2011_05
Patent number
US07947711B2

Reaction notes

Loading…