Phosphate → HCID 20708401, compound

HRID 430798Notes

Reaction equation

HRID 430798 reaction equation
[N:1]([CH2:4][CH2:5][N:6]1[C:14]2[C:9](=[C:10]([O:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])[CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7]1)=[N+]=[N-].[H][H].C(=O)([O-])[O-].[K+].[K+].[C:29]1([CH:35](Br)[C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.P([O-])([O-])([O-])=O>C(O)C.C1COCC1.C(#N)C.[Pd].O>[C:29]1([CH:35]([C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[NH:1][CH2:4][CH2:5][N:6]2[C:14]3[C:9](=[C:10]([O:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])[CH:11]=[CH:12][CH:13]=3)[CH:8]=[CH:7]2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

11

Reactant 5

HCID 1061PhosphateHCID 11430Potassium CarbonateHCID 236603BromodiphenylmethaneHCID 20708400HCID 20708400, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 20708401HCID 20708401, compoundYield 32%

Reagents, catalysts & solvents 5

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Procedure

Under argon atmosphere, methyl (1-(2-(azido)ethyl)indole-4-yloxy)acetate (432 mg) was dissolved in a mixed solvent of ethanol (10 ml) and THF (1 ml), and the obtained solution was stirred at room temperature. To this solution, 5% Pd/C (68 mg) was added and the atmosphere in the reaction vessel was replaced with hydrogen. After confirming vanishment of the materials, the atmosphere in the reaction vessel was replaced with argon. Solids were removed by filtration through Celite, and the solvent was removed under reduced pressure to obtain a crude product (362 mg). Under argon atmosphere, the crude product (40 mg) was dissolved in acetonitrile and the obtained solution was stirred at room temperature. To this solution, potassium carbonate (24 mg) and diphenylmethyl bromide (48 mg) were added and the resulting mixture was stirred at room temperature. After confirming vanishment of the materials, phosphate buffer (pH 7, 2 ml) and water (5 ml) were added to the reaction mixture, and the resultant was extracted three times with ethyl acetate (10 ml). The organic layers were combined and washed with saturated brine, followed by drying over sodium sulfate. After removing the sodium sulfate by filtration, the solvent was removed under reduced pressure and the residue was purified by column chromatography (solvent: hexane/ethyl acetate=3/1) using silica gel to obtain the desired compound (23 mg, yield: 32%).

Workup

  1. customSolids were removed by filtration through Celite
  2. customthe solvent was removed under reduced pressure
  3. customto obtain a crude product (362 mg)
  4. stirringthe obtained solution was stirred at room temperature
  5. stirringthe resulting mixture was stirred at room temperature
  6. additionwere added to the reaction mixture
  7. extractionthe resultant was extracted three times with ethyl acetate (10 ml)
  8. washwashed with saturated brine
  9. dry with materialby drying over sodium sulfate
  10. customAfter removing the sodium sulfate
  11. filtrationby filtration
  12. customthe solvent was removed under reduced pressure
  13. customthe residue was purified by column chromatography (solvent: hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-b29f2196318641e8a8a3918c9f4c9a67
Source dataset
uspto-grants-2001_11
Patent number
US06323235B1

Reaction notes

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