2-Propenoic acid, 2-azido-3-(3,4,5-trimethoxyphenyl)-, methyl ester → methyl 5,6,7-trimethoxy-1H-indole-2-carboxylate

HRID 720327

Reaction equation

HRID 720327 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:13]=[C:14]([N:19]=[N+]=[N-])[C:15]([O:17][CH3:18])=[O:16])[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10]>C1(C)C(C)=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:6](=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10])[NH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13]2

Participants

3

Reactant 1

HCID 43062472-Propenoic acid, 2-azido-3-(3,4,5-trimethoxyphenyl)-, methyl ester

Product 1

HCID 4453649methyl 5,6,7-trimethoxy-1H-indole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent2×

Procedure

Xylene (15 mL) was placed in a three-necked flask and stirred under reflux, and a xylene solution (30 mL) of methyl 3-(3,4,5-trimethoxyphenyl)-2-azidopropenoate (1.2 g) was added dropwise over 3 hours. The reaction mixture was refluxed for 1 hour and concentrated under reduced pressure. Water was added to the residue to conduct extraction with ethyl acetate. The extract was washed with water and saturated brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:3) to obtain the title compound.

Workup

  1. temperatureunder reflux
  2. temperatureThe reaction mixture was refluxed for 1 hour
  3. concentrationconcentrated under reduced pressure
  4. additionWater was added to the residue
  5. extractionextraction with ethyl acetate
  6. washThe extract was washed with water and saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:3)

Sources & evidence

ORD record
ord-306e5ab18e0d4f49a254e104fc7a273f
Source dataset
uspto-grants-2006_11
Patent number
US07135473B2

Linked notes

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