Water → 3-(6-Methoxy-7-oxiranylmethoxy-quinolin-4-yloxy)-5,6,6'-trimethyl-[2,2']bipyridine

HRID 229071Notes

Reaction equation

HRID 229071 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[OH:13])[N:9]=[CH:8][CH:7]=[C:6]2[O:14][C:15]1[C:16]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([CH3:29])[N:24]=2)=[N:17][C:18]([CH3:22])=[C:19]([CH3:21])[CH:20]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:36]([CH:38]1[O:40][CH2:39]1)Br.O>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH2:36][CH:38]1[CH2:39][O:40]1)[N:9]=[CH:8][CH:7]=[C:6]2[O:14][C:15]1[C:16]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([CH3:29])[N:24]=2)=[N:17][C:18]([CH3:22])=[C:19]([CH3:21])[CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 18430EpibromohydrinHCID 1361316246-Methoxy-4-(5,6,6'-trimethyl-[2,2']bipyridin-3-yloxy)-quinolin-7-ol2×

Product 1

HCID 577565913-(6-Methoxy-7-oxiranylmethoxy-quinolin-4-yloxy)-5,6,6'-trimethyl-[2,2']bipyridineYield 99%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-Methoxy-4-(5,6,6′-trimethyl-[2,2′]bipyridin-3-yloxy)-quinolin-7-ol (compound 443) (87 mg) was dissolved in N,N-dimethylformamide (4 ml) to prepare a solution, and potassium carbonate (93 mg) and epibromohydrin (0.06 ml) were added to the solution. The mixture was stirred at room temperature overnight. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was then washed with saturated brine and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by thin layer chromatography using chloroform-methanol to give the title compound (97 mg, yield 99%).

Workup

  1. additionwere added to the solution
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was then washed with saturated brine
  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 thin layer chromatography

Sources & evidence

ORD record
ord-8c93813056174ee2a15b4c182d518ba0
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

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