Triethylsilane → HCID 59332633, compound

HRID 387273Notes

Reaction equation

HRID 387273 reaction equation
[CH3:1][CH:2]1[CH2:7][C:6](=O)[CH2:5][CH:4]([CH3:9])[S:3]1.[Si](OS(C(F)(F)F)(=O)=O)(C)(C)C.[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>ClCCl>[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[CH2:7][CH:2]([CH3:1])[S:3][CH:4]([CH3:9])[CH2:5]1

Participants

6

Reactant 4

HCID 12052TriethylsilaneHCID 65367Trimethylsilyl triflateHCID 137817942323-17-3HCID 59332585Ethyl 5-bromo-1H-indole-7-carboxylate

Product 1

HCID 59332633HCID 59332633, compoundYield 26.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

2,6-Dimethyltetrahydro-4H-thiopyran-4-one (0.293 g, 2.03 mmol) was dissolved in dichloromethane (35 mL) in an oven dried flask containing 3 Å molecular sieves and stirred under argon at 0° C. TMS-OTf (0.451 g, 2.0 mmol, 0.36 mL) was added slowly to the mixture over 10 min. Ethyl 5-bromo-1H-indole-7-carboxylate (0.293 g, 2.031 mmol) was dissolved in DCM (10 mL) and added to the reaction via syringe pump over 2 hours, after which it was stirred for 3 hours between 0 and 10° C. The reaction was cooled to 0° C. and triethylsilane (0.353 g, 0.485 mL, 3.04 mmol) was then added all at once and the reaction was stirred at room temperature overnight. The reaction was then quenched with a saturated sodium bicarbonate solution, filtered, then extracted with DCM. The combined organics were washed with water. The combined aqueous layers were back-extracted with DCM. The combined organics were washed with brine, dried with MgSO4, and concentrated. The crude compound was purified on Combiflash silica column with 0-30% EA/DCM to give 0.212 g (26%) of the title compound.

Workup

  1. customdried flask
  2. additioncontaining 3 Å molecular sieves
  3. additionadded to the reaction via syringe pump over 2 hours
  4. stirringafter which it was stirred for 3 hours between 0 and 10° C
  5. temperatureThe reaction was cooled to 0° C.
  6. stirringwas stirred at room temperature overnight
  7. customThe reaction was then quenched with a saturated sodium bicarbonate solution
  8. filtrationfiltered
  9. extractionextracted with DCM
  10. washThe combined organics were washed with water
  11. extractionThe combined aqueous layers were back-extracted with DCM
  12. washThe combined organics were washed with brine
  13. dry with materialdried with MgSO4
  14. concentrationconcentrated
  15. customThe crude compound was purified on Combiflash silica column with 0-30% EA/DCM

Sources & evidence

ORD record
ord-16dfc7a79a8646d2a4910504ae8b40ff
Source dataset
uspto-grants-2013_02
Patent number
US08372875B2

Reaction notes

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