Triethylsilane → methyl 5-bromo-3-(4-thiepanyl)-1H-indole-7-carboxylate
Reaction equation
[S:1]1[CH2:7][CH2:6][CH2:5][C:4](=O)[CH2:3][CH2:2]1.[Si](OS(C(F)(F)F)(=O)=O)(C)(C)C.[Br:21][C:22]1[CH:23]=[C:24]2[C:28](=[C:29]([C:31]([O:33][CH3:34])=[O:32])[CH:30]=1)[NH:27][CH:26]=[CH:25]2.C([SiH](CC)CC)C>C(Cl)Cl>[Br:21][C:22]1[CH:23]=[C:24]2[C:28](=[C:29]([C:31]([O:33][CH3:34])=[O:32])[CH:30]=1)[NH:27][CH:26]=[C:25]2[CH:4]1[CH2:5][CH2:6][CH2:7][S:1][CH2:2][CH2:3]1Participants
Procedure
To a flask under argon in an ice-bath, the 4-thiepanone (200 mg, 1.536 mmol) in 6 mL of dried CH2Cl2 was first dried w/4 A sieves and then transferred via a double needle tubing (cannula). TMS-OTf (278 uL, 1.536 mmol) was added dropwise and the reaction was stirred for 10 min. A solution of methyl 5-bromo-1H-indole-7-carboxylate (390 mg, 1.536 mmol) in 7 mL of CH2Cl2 was dried with 4 A sieves and then added into above solution dropwise. Stirring continued for 4 hours and the reaction was warmed to room temperature. The mixture was cooled to 0° C. and triethylsilane (245 uL, 1.536 mmol) was added as one portion. The mixture was stirred overnight then warmed to room temperature. The mixture was quenched water and sat. NaHCO3, then diluted water/AcOEt and washed with H2O and brine. 194 mg of crude product was obtained.
Workup
- additionadded into above solution dropwise
- stirringStirring
- waitcontinued for 4 hours
- temperatureThe mixture was cooled to 0° C.
- stirringThe mixture was stirred overnight
- temperaturethen warmed to room temperature
- customThe mixture was quenched water and sat. NaHCO3
- washdiluted water/AcOEt and washed with H2O and brine
Sources & evidence
- ORD record
- ord-66a71348ceb742b7a75b84aee0a3e8f2
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08372875B2
Reaction notes
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