تفاعل #1869158

ord-65c80db4378345879329b129a789998c

معادلة التفاعل

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
المردود 82.0%

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    أخرىIt is then evaporated to dryness
  2. 2
    workup.DISSOLUTIONdissolved in ethyl acetate
  3. 3
    غسيلThe organic phase is washed with water
  4. 4
    أخرىa saturated solution of sodium bicarbonate, it is separated
  5. 5
    تجفيفdried with anhydrous sodium sulphate
  6. 6
    أخرىThe organic solution is evaporated to dryness
  7. 7
    غسيلthe resulting solid is repeatedly washed with ethyl ether

الإجراء التجريبي

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.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US07498328B2uspto-grants-2009_03