HCID 57942129, compound → HCID 57942158, compound

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[C:13]([C:19](=[O:30])[C:20]3[C:25]([N+:26]([O-])=O)=[CH:24][CH:23]=[CH:22][C:21]=3[Cl:29])=[N:14][CH:15]=[C:16]([Cl:18])[CH:17]=2)(=[O:10])=[O:9])=[CH:4][C:3]=1[C:31]([F:34])([F:33])[F:32]>C(O)(=O)C.CCOC(C)=O.[Fe]>[NH2:26][C:25]1[CH:24]=[CH:23][CH:22]=[C:21]([Cl:29])[C:20]=1[C:19]([C:13]1[C:12]([NH:11][S:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([C:31]([F:34])([F:33])[F:32])[CH:4]=2)(=[O:10])=[O:9])=[CH:17][C:16]([Cl:18])=[CH:15][N:14]=1)=[O:30]

Participants

Procedure

A 50 mL round-bottom flask was charged with 4-chloro-N-(5-chloro-2-(2-chloro-6-nitrobenzoyl)pyridin-3-yl)-3-(trifluoromethyl) benzenesulfonamide (350 mg, 0.63 mmol), iron powder (560 mg, 10 mmol) in acetic acid (30 mL) and stirred at room temperature for 2 h and then at 50° C. for 30 min. After cooling, the reaction mixture was diluted with EtOAc, filtered through Celite and evaporated the solvent in vacuo. The residue was dissolved in EtOAc and washed with NaHCO3 (sat), brine, dried over MgSO4, and concentrated under reduced pressure and was further purified through automated normal-phase chromatography to afford the title compound: 1H NMR (400 MHz, CDCl3) δ 10.60 (s, 1 H), 8.28 (d, 1 H), 8.20 (d, 1 H), 8.16 (d, 1 H), 7.96 (dd, 1 H), 7.60 (d, 1 H), 7.09 (t, 1 H), 6.64 (dd, 2H), 4.40 (bs, 2H); MS (ES) (M+H)+ expected 523.9, found 523.9.