2-Methylpyridine → 1-[2-(6,7-Dimethoxy-quinolin-4-yloxy)-5-methoxyphenyl]-2-pyridin-2-yl-ethanol

HRID 228692Notes

Reaction equation

HRID 228692 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH3:7].C([Li])CCC.[CH3:13][O:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][C:24]=1[O:25][CH3:26])[N:21]=[CH:20][CH:19]=[C:18]2[O:27][C:28]1[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][C:29]=1[CH:30]=[O:31].[Cl-].[NH4+]>O1CCCC1>[CH3:13][O:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][C:24]=1[O:25][CH3:26])[N:21]=[CH:20][CH:19]=[C:18]2[O:27][C:28]1[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][C:29]=1[CH:30]([OH:31])[CH2:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1

Participants

6

Reactant 4

HCID 79752-MethylpyridineHCID 25517Ammonium ChlorideHCID 230782792-[(6,7-Dimethoxy-4-quinolyl)oxy]-5-methoxybenzaldehydeHCID 178418339Butyllithium

Product 1

HCID 577565671-[2-(6,7-Dimethoxy-quinolin-4-yloxy)-5-methoxyphenyl]-2-pyridin-2-yl-ethanolYield 29%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

2-Picoline (40 μl) was dissolved in tetrahydrofuran (2 ml), and the solution was cooled to −78° C. under an argon atmosphere. n-Butyllithium (1.56 M hexane solution) (260 μl) was added to the cooled solution, and the mixture was stirred for 2 hr. A solution of 2-(6,7-dimethoxy-quinolin-4-yloxy)-5-methoxy-benzaldehyde (100 mg) in tetrahydrofuran (2 ml) was then added to the reaction solution, and the mixture was stirred at −78° C. for one hr. A saturated ammonium chloride solution was added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was then washed with water and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by column chromatography using acetone-hexane to give the title compound (37 mg, yield 29%).

Workup

  1. stirringthe mixture was stirred at −78° C. for one hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was then washed with water
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. customThe solvent was removed by distillation under the reduced pressure
  6. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-fc1a29d379b0497d8389e76f45bcde67
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

Loading…