Реакция #595325

ord-182caf2807d84ef799efe0560e10dc7d

Уравнение реакции

Nc1c(F)cc(F)c(F)c1Nc1ccc(I)cc1F
3,5,6-trifluoro-N1-(2-fluoro-4-iodophenyl)benzene-1,2-diamine
O=S(=O)(Cl)Cl
sulfonyl chloride
C=CCC1(S(=O)(=O)Cl)CC1
1-allyl-cyclopropanesulfonyl chloride
C=CCC1(S(=O)(=O)Nc2c(F)cc(F)c(F)c2Nc2ccc(I)cc2F)CC1
1-Allyl-cyclopropanesulfonic acid [3,4,6-trifluoro-2-(2-fluoro-4-iodo-phenylamino)phenyl]-amide

Растворители

Условия реакции

Температура
40°CELSIUS
Подробные условия
See reaction.notes.procedure_details.

Обработка

  1. 1
    ДругоеThe reaction mixture was partitioned with water and EtOAc
  2. 2
    ПромывкаThe organic layer was washed with brine
  3. 3
    Другоеdried (MGSO4)
  4. 4
    Концентрированиеconcentrated under reduced pressure
  5. 5
    ДругоеThe residue was purified by flash column chromatography on silica

Методика

To a stirred solution of the amine, i.e., 3,5,6-trifluoro-N1-(2-fluoro-4-iodophenyl)benzene-1,2-diamine, (1 eq) in anhydrous pyridine (5 ml/mmole) was added the sulfonyl chloride, i.e., 1-allyl-cyclopropanesulfonyl chloride, (1-5 eq). The reaction mixture was stirred at 40° C. for 48 hours. The reaction mixture was partitioned with water and EtOAc. The organic layer was washed with brine, dried (MGSO4) and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica. 1H NMR (CDCl3, 300 MHz): δ 7.41 (dd, 1H), 7.38 (dd, 1H), 7.09 (s, 1H), 6.78 (m, 1H), 6.49 (m, 1H), 5.96 (s, 1H), 5.86 (m, 1H), 5.18 (d, 2H), 2.76 (d, 2H), 1.23 (m, 2H), 0.872 (m, 2H).

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US09095581B2uspto-grants-2015_08