1-Bromo-2-Chloroethane → HCID 57756475, compound

HRID 229066Notes

Reaction equation

HRID 229066 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([O:12][C:13]3[C:14]([CH3:23])=[N:15][C:16]4[C:21]([CH:22]=3)=[CH:20][CH:19]=[CH:18][N:17]=4)=[CH:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[O:24][CH3:25].C(=O)([O-])[O-].[K+].[K+].Br[CH2:33][CH2:34]Cl.[NH:36]1[CH2:41][CH2:40][O:39][CH2:38][CH2:37]1>CN(C)C=O.O>[CH3:25][O:24][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:2]=1[O:1][CH2:40][CH2:41][N:36]1[CH2:34][CH2:33][O:39][CH2:38][CH2:37]1)[N:9]=[CH:8][CH:7]=[C:6]2[O:12][C:13]1[C:14]([CH3:23])=[N:15][C:16]2[C:21]([CH:22]=1)=[CH:20][CH:19]=[CH:18][N:17]=2

Participants

7

Reactant 4

HCID 78491-Bromo-2-ChloroethaneHCID 8083Morpholine2×HCID 11430Potassium Carbonate2×HCID 1363851103-[7-Hydroxy-6-methoxy-quinolin-4-yloxy]-2-methyl-[1,8]naphthyridine

Product 1

HCID 57756475HCID 57756475, compoundYield 12%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

3-[7-Hydroxy-6-methoxy-quinolin-4-yloxy]-2-methyl-[1,8]naphthyridine (67 mg) was dissolved in N,N-dimethylformamide (5 ml) to prepare a solution. Potassium carbonate (225 mg) and 1-bromo-2-chloroethane (0.15 ml) were added to the solution, and the mixture was stirred at room temperature overnight. Morpholine (0.3 ml) was added to the reaction solution, and the mixture was further stirred overnight at 70° C. Potassium carbonate (354 mg) and morpholine (0.2 ml) were further added to the reaction solution, and the mixture was stirred at 70° C. overnight. The reaction solution was cooled to room temperature, water was then added to the reaction solution, and the mixture was extracted with chloroform. The chloroform layer was 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 (11 mg, yield 12%) (2 steps).

Workup

  1. customto prepare a solution
  2. waitthe mixture was further stirred overnight at 70° C
  3. stirringthe mixture was stirred at 70° C. overnight
  4. temperatureThe reaction solution was cooled to room temperature
  5. extractionthe mixture was extracted with chloroform
  6. washThe chloroform layer was washed with saturated brine
  7. dry with materialwas dried over anhydrous sodium sulfate
  8. customThe solvent was removed by distillation under the reduced pressure
  9. customthe residue was purified by thin layer chromatography

Sources & evidence

ORD record
ord-2dc6df13b63c4e06ab669de554e89b90
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

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