Sodium methanethiolate → 5-Chloro-N-[1-[2-(methylthio)ethyl]-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-1H-indole-2-carboxamide

Temperature

80 °C

Sodium thiomethoxide (280 mg, 4.00 mmol) and KI (10 mg, 0.06 mmol) were added to a soluton of 5-chloro-N-[1-(2-chloroethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-1H-indole-2-carboxamide (Method 3; 1.07 g, 2.67 mmol) in DMF (10 mL) under an inert atmosphere and heated at 80° C. for 2 hours. On cooling the mixture was diluted with EtOAc (100 mL), washed with water (20 mL), dried (Na2SO4), filtered and evaporated. The residue was purified by column chromatography (DCM to DCM:THF (2:23)) to give a white solid. The solid was triturated with refluxing Et2O (20 mL) and the solid filtered, washed with Et2O (10 mL) then hexane (10 mL) to afford the title compound (410 mg, 37%) as an off white solid.

1. temperatureOn cooling the mixture
2. washwashed with water (20 mL)
3. dry with materialdried (Na2SO4)
4. filtrationfiltered
5. customevaporated
6. customThe residue was purified by column chromatography (DCM to DCM:THF (2:23))
7. customto give a white solid
8. customThe solid was triturated with refluxing Et2O (20 mL)
9. filtrationthe solid filtered
10. washwashed with Et2O (10 mL)

ORD record

ord-b5ab8dd6c7204ea9806a9f225baba0a8

Source dataset

uspto-grants-2007_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07169927B2