tert-Butyldimethylsilyl chloride → HCID 54418023, compound

To a solution of (S)-5-bromo-3-[(N-methylpyrrolidin-2-yl)methyl]-l H-indole (Example 3c, 1.00 g, 3.41 mmol) in THF (15 mL) under argon, was added sodium hexamethyldisilazide (6.82 mL, 6.82 mmol and the resulting solution was stirred at room temperature for 20 min. The reaction mixture was cooled to 0° C. and to this was added a solution of t-butydimethylsilyl chloride (1.03 g, 6.82 mmol) in THF (4 mL) and the resulting culture was warmed to room temperature and stirred for 1 hour. The solvent as removed in vacuo and the resulting product was diluted with water (10 mL) and extracted with ethyl acetate (2×10 mL). The ethyl acetate extract was washed with brine (10 mL), dried (Na2SO4), filtered and the filtrate was evaporated to dryness. The crude residue was subjected to flash silica gel chromography to afford the title compound as a yellow oil (1.07 g, 79%). 13C NMR (CDCl3)δ: 140.1, 133.1, 129.8, 124.1, 121.5, 115.8, 115.2, 112.7, 66.2, 7.6, 40.9, 31.6, 30.1, 26.2, 21.9, 19.5, −3.96

1. temperatureThe reaction mixture was cooled to 0° C.
2. temperaturethe resulting culture was warmed to room temperature
3. stirringstirred for 1 hour
4. customThe solvent as removed in vacuo
5. additionthe resulting product was diluted with water (10 mL)
6. extractionextracted with ethyl acetate (2×10 mL)
7. extractionThe ethyl acetate extract
8. washwas washed with brine (10 mL)
9. dry with materialdried (Na2SO4)
10. filtrationfiltered
11. customthe filtrate was evaporated to dryness

ORD record

ord-c0ced1bf0ae943769994578b186ea2c8

Source dataset

uspto-grants-2001_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06329390B1