反应 #1869158

ord-65c80db4378345879329b129a789998c

反应方程式

CN(C)CCc1c[nH]c2ccc(N)cc12
5-amino-3-(2-dimethylaminoethyl)-1H-indol
Cc1c(S(=O)(=O)Cl)sc2ccc(Cl)cc12
5-chloro-3-methyl-benzo[b]thiophene-2-sulphonyl chloride
Cc1c(S(=O)(=O)Nc2ccc3[nH]cc(CCN(C)C)c3c2)sc2ccc(Cl)cc12
N-[3-(2-dimethylaminoethyl)-1H-indol-5-yl]-5-chloro-3-methyl-benzo[b]thiophene-2-sulphonamide
收率 82.0%

反应条件

详细条件
See reaction.notes.procedure_details.

后处理

  1. 1
    其他It is then evaporated to dryness
  2. 2
    workup.DISSOLUTIONdissolved in ethyl acetate
  3. 3
    洗涤The organic phase is washed with water
  4. 4
    其他a saturated solution of sodium bicarbonate, it is separated
  5. 5
    干燥dried with anhydrous sodium sulphate
  6. 6
    其他The organic solution is evaporated to dryness
  7. 7
    洗涤the resulting solid is repeatedly washed with ethyl ether

实验过程

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.

来源

DOI: 10.6084/m9.figshare.5104873.v1专利: US07498328B2uspto-grants-2009_03