Triethylsilane → Ethyl 5-bromo-3-(tetrahydro-3-thienyl)-1H-indole-7-carboxylate

Temperature

0 °C

Dihydro-3(2H)-thiophenone (0.381 g, 3.73 mmol) was dissolved in dichloromethane (50 ml) in an oven dried flask containing 3 Å molecular sieves and stirred under Argon at 0° C. TMS-OTf (0.826 g, 3.73 mmol, 0.67 mL) was added slowly to the mixture over 10 min. Ethyl 5-bromo-1H-indole-7-carboxylate (1 g, 3.73 mmol) was dissolved in DCM (6 mL) and added to the reaction via syringe pump over 2 hours, after which it was stirred for 30 min at 0° C. Triethylsilane (0.651 g, 0.89 ml, 5.59 mmol) was then added all at once and the reaction was stirred at room temperature for 18 hours. The reaction was then quenched with a saturated sodium bicarbonate solution (35 mL) and extracted with DCM (2×50 mL). The combined organics were washed with water (2×100 mL), brine, dried with MgSO4, and concentrated. The crude compound was purified on Combiflash silica column with 10% EA/Hexane to give 0.620 g (47%) of the title compound.

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 30 min at 0° C
5. stirringwas stirred at room temperature for 18 hours
6. customThe reaction was then quenched with a saturated sodium bicarbonate solution (35 mL)
7. extractionextracted with DCM (2×50 mL)
8. washThe combined organics were washed with water (2×100 mL), brine
9. dry with materialdried with MgSO4
10. concentrationconcentrated
11. customThe crude compound was purified on Combiflash silica column with 10% EA/Hexane

ORD record

ord-ddd5252f50984bb893e8191037555c78

Source dataset

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08071584B2