Iodine → HCID 9895034, compound

Reaction equation

[I:1]I.N[C:4]1[C:8]([CH:9]2[CH2:11][C:10]2([Br:13])[Br:12])=[CH:7][N:6]([C:14]2[C:19]([Cl:20])=[CH:18][C:17]([C:21]([F:24])([F:23])[F:22])=[CH:16][C:15]=2[Cl:25])[N:5]=1.N(OC(C)(C)C)=O>ClCCl>[Br:12][C:10]1([Br:13])[CH2:11][CH:9]1[C:8]1[C:4]([I:1])=[N:5][N:6]([C:14]2[C:19]([Cl:20])=[CH:18][C:17]([C:21]([F:24])([F:23])[F:22])=[CH:16][C:15]=2[Cl:25])[CH:7]=1

Participants

Procedure

Iodine (0.55 g) was added to a stirred solution of the title compound of Example 8 (0.40 g) in dichioromethane (10 ml), followed by the dropwise addition of t-butyl nitrite (0.21 g). The reaction mixture was stirred at room temperature for 2 hours, then partitioned between dichloromethane and aqueous sodium thiosulphate solution and the organic phase separated, dried and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel, using hexane and then dichloromethane as eluants, followed by reverse phase HPLC on C18 silica, using a mixture of acetonitrile:water:methanol (30:60:10) as eluant, to produce the title compound as an off-white foam. δ (CDCl3): 1.84 (t,1H), 2.26 (dd,1H), 2.67 (dd,1H), 7.20 (s,1H), 7.72 (s,2H). MS (thermospray): M/Z [M+H] 602.4; C13H6Br2Cl2F3IN2 +H requires 602.74.