Potassium Carbonate → (E)-N-{4-[2-(1H-indazol-3-yl)vinyl]-3-nitrophenyl}-N-(2-methoxyethyl)-2-morpholinoethylamine

HRID 1821402Notes

Reaction equation

HRID 1821402 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1.[CH3:13][O:14][CH2:15][CH2:16][NH:17][CH2:18][CH2:19][N:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1.[Br-].[NH:27]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:29]([CH2:36][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[N:28]1.C(=O)([O-])[O-].[K+].[K+]>O.CS(C)=O>[NH:27]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:29](/[CH:36]=[CH:6]/[C:5]2[CH:8]=[CH:9][C:2]([N:17]([CH2:18][CH2:19][N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)[CH2:16][CH2:15][O:14][CH3:13])=[CH:3][C:4]=2[N+:10]([O-:12])=[O:11])=[N:28]1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 762264-Fluoro-2-nitrobenzaldehydeHCID 23116487N-(2-methoxyethyl)-2-morpholinoethylamineHCID 178419401HCID 178419401, compound

Product 1

HCID 69004424(E)-N-{4-[2-(1H-indazol-3-yl)vinyl]-3-nitrophenyl}-N-(2-methoxyethyl)-2-morpholinoethylamineYield 20%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×

Conditions

Temperature
100 °C

Procedure

4-Fluoro-2-nitrobenzaldehyde (0.20 g, 1.2 mmol), N-(2-methoxyethyl)-2-morpholinoethylamine (1.2 g, 6.5 mmol) and DMSO (3.5 mL) were added and stirred at 100° C. for 3 hours. The reaction mixture was added with water and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1 to ethyl acetate). In a similar manner to Example 1, the obtained 4-[N-(2-methoxyethyl)-N-(2-morpholinoethyl)amino]-2-nitrobenzaldehyde was dissolved in methanol (8.0 mL) and the solution was added with (1H-indazol-3-ylmethyl)triphenylphosphonium bromide (0.21 g, 0.62 mmol) and potassium carbonate (0.17 g, 1.3 mmol) followed by stirring at room temperature for 1 hour. The reaction mixture was added with water and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform to chloroform/methanol=9/1) to obtain (E)-N-{4-[2-(1H-indazol-3-yl)vinyl]-3-nitrophenyl}-N-(2-methoxyethyl)-2-morpholinoethylamine (45 mg, 20%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1 to ethyl acetate)
  6. dissolutionIn a similar manner to Example 1, the obtained 4-[N-(2-methoxyethyl)-N-(2-morpholinoethyl)amino]-2-nitrobenzaldehyde was dissolved in methanol (8.0 mL)
  7. stirringby stirring at room temperature for 1 hour
  8. extractionextracted with ethyl acetate
  9. washThe organic layer was washed with water and saturated brine
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customthe solvent was evaporated under reduced pressure
  12. customThe residue was purified by silica gel column chromatography (chloroform to chloroform/methanol=9/1)

Sources & evidence

ORD record
ord-d05a919d3150479290522ecee62199de
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

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