Triethylsilane → 5-bromo-3-(2,2-dimethyltetrahydro-thiopyran-4-yl)-1H-indole-7-carboxylic acid ethyl ester

HRID 387280Notes

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]1

Participants

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-958813287f3c4c08b24acfcf288f37f8
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08372875B2

Reaction notes

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