2-Mesitylenesulfonyl chloride → 2,4,6-Trimethyl-N-[2,2,2-trifluoro-1-(1H-indol-3-ylmethyl)ethyl]benzenesulfonamide

Temperature

45 °C

A mixture of 42 mg (0.18 mmol) of 2,2,2-trifluoro-1-(1H-indol-3-ylmethyl)ethylamine and 45 mg, 0.21 mmol) of mesitylenesulfonyl chloride in 0.5 mL of pyridine was warmed to 45° C. The reaction was monitored by thin layer chromatography (ethyl acetate-hexanes (3:7)) indicating a new less polar product compared to the amine. After 6 hours, the mixture was cooled and diluted with 7 mL of 1 N aqueous HCl and extracted with three 7 mL portions of ethyl acetate. The combined organic layers were washed with three 5 mL portions of 1 N aqueous HCl, 5 mL of brine, three 5 mL portions of saturated aqueous sodium bicarbonate, dried over magnesium sulfate, filtered, and concentrated in vacuo to afford 62 mg (82.1%) of crude solid. The crude material was adsorbed onto silica gel and chromatographed on silica gel using dichloromethane-hexanes (gradient: 50%-100%). The material from the column was crystallized from ether-hexanes to afford 52 mg (67%) of the title compounds as a white solid, m.p. 189° C.-191° C.; MS: m/z 409.15 (M−).

1. temperaturethe mixture was cooled
2. extractionextracted with three 7 mL portions of ethyl acetate
3. washThe combined organic layers were washed with three 5 mL portions of 1 N aqueous HCl, 5 mL of brine, three 5 mL portions of saturated aqueous sodium bicarbonate
4. dry with materialdried over magnesium sulfate
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customto afford 62 mg (82.1%) of crude solid
8. customchromatographed on silica gel
9. customThe material from the column was crystallized from ether-hexanes

ORD record

ord-251cb68304314dcc9226e5c3d1bbce9f

Source dataset

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07741361B2