Ethyl 2-azido-3-(4-trimethylsilylphenyl)propenoate → ethyl 6-trimethylsilyl-1H-indole-2-carboxylate
Reaction equation
[N:1]([C:4](=[CH:10][C:11]1[CH:16]=[CH:15][C:14]([Si:17]([CH3:20])([CH3:19])[CH3:18])=[CH:13][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6])=[N+]=[N-]>C1(C)C=CC=CC=1.FC(F)(F)C(F)(F)C(F)(F)C([O-])=O.[Rh+3].[Rh+3].FC(F)(F)C(F)(F)C(F)(F)C([O-])=O.FC(F)(F)C(F)(F)C(F)(F)C([O-])=O.FC(F)(F)C(F)(F)C(F)(F)C([O-])=O.FC(F)(F)C(F)(F)C(F)(F)C([O-])=O.FC(F)(F)C(F)(F)C(F)(F)C([O-])=O>[CH3:18][Si:17]([CH3:20])([CH3:19])[C:14]1[CH:15]=[C:16]2[C:11]([CH:10]=[C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[NH:1]2)=[CH:12][CH:13]=1Participants
4
Conditions
- Temperature
- 70 °C
Procedure
0.17 g (0.16 mmol) of the dirhodium heptafluorobutyrate dimer complex is added to a solution of 1.0 g (3.14 mmol) of ethyl 2-azido-3-(4-trimethylsilylphenyl)propenoate obtained in stage 1.1, in 20 ml of dry toluene, maintained under an inert atmosphere. The reaction mixture is then stirred for 12 h at 70° C. After a return to ambient temperature, the reaction mixture is filtered through silica gel, elution being carried out with ethyl acetate. The filtrate is subsequently concentrated under reduced pressure. The residue is purified by silica gel column chromatography, elution being carried out with a mixture of heptane and dichloromethane. 0.61 g of the expected product is isolated in the form of a beige powder.
Workup
- temperaturemaintained under an inert atmosphere
- filtrationAfter a return to ambient temperature, the reaction mixture is filtered through silica gel, elution
- concentrationThe filtrate is subsequently concentrated under reduced pressure
- customThe residue is purified by silica gel column chromatography, elution
- additionbeing carried out with a mixture of heptane and dichloromethane
Sources & evidence
- ORD record
- ord-75923eb99c2c43689c49bcae52d89e23
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08399491B2
Reaction notes
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