Triethylsilane → Ethyl 5-Bromo-3-[2-(1-methylethyl)tetrahydro-2H-thiopyran-4-yl]-1H-indole-7-carboxylate

2-(1-methylethyl)tetrahydro-2H-thiopyran-4-one (1.185 g, 7.49 mmol) was dissolved in dry dichloromethane (DCM) (20 mL), cooled in an ice bath to ca 0° C., and stirred under argon. Trimethylsilyl trifluoromethanesulfonate (2.71 mL, 14.98 mmol) was added dropwise over 10 minutes, and dry DCM (5 mL) was used to wash in the last of the trimethylsilyltrifluoromethanesulfonate. To this mixture was added dropwise, a solution of ethyl 5-bromo-1H-indole-7-carboxylate (2.145 g, 8 mmol) in dry DCM (20 mL), and then an additional portion of dry DCM (5 mL) was used to wash the last of ethyl 5-bromo-1H-indole-7-carboxylate into the reaction. Triethylsilane (4.77 mL, 30.0 mmol) was added to the reaction in one portion. The resulting mixture was stirred 2 h at 0° C., and left stirring at 23° C. overnight. The reaction was diluted with saturated aqueous sodium bicarbonate, and the resulting biphasic mixture was extracted with DCM, dried (MgSO4) and the DCM was removed in vacuo to give the title compound as a dark yellow oil.

1. temperaturecooled in an ice bath to ca 0° C.
2. washto wash in the last of the trimethylsilyltrifluoromethanesulfonate
3. additionTo this mixture was added dropwise
4. washto wash the last of ethyl 5-bromo-1H-indole-7-carboxylate
5. custominto the reaction
6. stirringThe resulting mixture was stirred 2 h at 0° C.
7. waitleft
8. stirringstirring at 23° C. overnight
9. extractionthe resulting biphasic mixture was extracted with DCM
10. dry with materialdried (MgSO4)
11. customthe DCM was removed in vacuo

ORD record

ord-3987989df0ee42e797b68917ef8a8834

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08372875B2