Triethylsilane → 5-bromo-3-(2,2-dimethyltetrahydro-thiopyran-4-yl)-1H-indole-7-carboxylic acid ethyl ester
Reaction equation
[CH3:1][C:2]1([CH3:9])[CH2:7][C:6](=O)[CH2:5][CH2:4][S:3]1.FC(F)(F)S(O[Si](C)(C)C)(=O)=O.[Br:22][C:23]1[CH:24]=[C:25]2[C:29](=[C:30]([C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH:31]=1)[NH:28][CH:27]=[CH:26]2.C([SiH](CC)CC)C>C(Cl)Cl>[Br:22][C:23]1[CH:24]=[C:25]2[C:29](=[C:30]([C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH:31]=1)[NH:28][CH:27]=[C:26]2[CH:6]1[CH2:5][CH2:4][S:3][C:2]([CH3:9])([CH3:1])[CH2:7]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
2,2-Dimethyltetrahydro-4H-thiopyran-4-one (0.675 g, 4.68 mmol) was placed in a dried flask fitted up with an addition funnel, a septum and an argon inlet, and dissolved in dry DCM (15 mL), cooled to 0° C., stirred, and then trimethylsilyl trifluoromethanesulfonate (1.692 mL, 9.36 mmol) was added dropwise through the addition funnel over 10 minutes. DCM (5 mL) was used to wash the addition funnel walls. To this mixture was added dropwise ethyl 5-bromo-1H-indole-7-carboxylate (1.341 g, 5 mmol) in DCM (15 mL) over 2 hours. Then triethylsilane (2.98 mL, 18.73 mmol) was added in one portion. The mixture was stirred 2 h at 0° C., and left stirring at 23° C. overnight. The reaction was quenched with a saturated aqueous solution of sodium bicarbonate, and the resulting biphasic mixture extracted with DCM to give 2.115 g of the title compound.
Workup
- customfitted up with an addition funnel
- washto wash the addition funnel walls
- stirringThe mixture was stirred 2 h at 0° C.
- waitleft
- stirringstirring at 23° C. overnight
- customThe reaction was quenched with a saturated aqueous solution of sodium bicarbonate
- extractionthe resulting biphasic mixture extracted with DCM
Sources & evidence
- ORD record
- ord-4c37376468dc4adbafe60eee88a045d3
- Source dataset
- uspto-grants-2011_12
- Patent number
- US08071584B2
Reaction notes
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