Reaction #1869158

Reaction equation

5-amino-3-(2-dimethylaminoethyl)-1H-indol

5-chloro-3-methyl-benzo[b]thiophene-2-sulphonyl chloride

→

N-[3-(2-dimethylaminoethyl)-1H-indol-5-yl]-5-chloro-3-methyl-benzo[b]thiophene-2-sulphonamide

Yield 82.0%

Solvents

pyridine

pyridine

Conditions

Workup

1. 1
   OtherIt is then evaporated to dryness
2. 2
   workup.DISSOLUTIONdissolved in ethyl acetate
3. 3
   WashThe organic phase is washed with water
4. 4
   Othera saturated solution of sodium bicarbonate, it is separated
5. 5
   Dryingdried with anhydrous sodium sulphate
6. 6
   OtherThe organic solution is evaporated to dryness
7. 7
   Washthe resulting solid is repeatedly washed with ethyl ether

Procedure

To a solution of 3.05 g (15 mMol) of 5-amino-3-(2-dimethylaminoethyl)-1H-indol in 100 ml of pyridine is added dropwise at ambient temperature a solution of 4.21 g (15 mMol) of 5-chloro-3-methyl-benzo[b]thiophene-2-sulphonyl chloride in 20 ml of pyridine. The reaction mixture is stirred at ambient temperature for 20 hours. It is then evaporated to dryness, slightly alkalinised with diluted ammonia and dissolved in ethyl acetate. The organic phase is washed with water and a saturated solution of sodium bicarbonate, it is separated and dried with anhydrous sodium sulphate. The organic solution is evaporated to dryness and the resulting solid is repeatedly washed with ethyl ether, to yield 5.5 g (82%) of N-[3-(2-dimethylaminoethyl)-1H-indol-5-yl]-5-chloro-3-methyl-benzo[b]thiophene-2-sulphonamide as a solid with m.p.=226-227° C.

Source