Reaction #595325

Reaction equation

3,5,6-trifluoro-N1-(2-fluoro-4-iodophenyl)benzene-1,2-diamine

sulfonyl chloride

1-allyl-cyclopropanesulfonyl chloride

→

1-Allyl-cyclopropanesulfonic acid [3,4,6-trifluoro-2-(2-fluoro-4-iodo-phenylamino)phenyl]-amide

Solvents

pyridine

Conditions

Workup

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

Procedure

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).

Source