[CH:1]([S:4]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:14]=[C:15]3[CH:21]=[CH:20][NH:19][C:16]3=[N:17][CH:18]=2)=[CH:9][CH:8]=1)(=[O:6])=[O:5])([CH3:3])[CH3:2].[I:22]Cl.ClCCl.CCOC(C)=O>N1C=CC=CC=1>[I:22][C:21]1[C:15]2[C:16](=[N:17][CH:18]=[C:13]([C:10]3[CH:9]=[CH:8][C:7]([S:4]([CH:1]([CH3:3])[CH3:2])(=[O:6])=[O:5])=[CH:12][CH:11]=3)[N:14]=2)[NH:19][CH:20]=1To 2-(4-isopropylsulfonylphenyl)-5H-pyrrolo[2,3-b]pyrazine (9 g, 29.86 mmol) in pyridine (90.00 mL) at RT was added a 1M solution of iodine monochloride in dichloromethane (32.85 mL of 1 M, 32.85 mmol). The resulting dark brown solution was stirred at RT for 4 hours then taken into EtOAc and washed with aqueous sodium thiosulphate/NaHCO3×2 then with brine, then dried over MgSO4 and concentrated under reduced pressure. The solid residue was triturated with acetonitrile, filtered and washed with acetonitrile, dried in vacuo to give the subtitle compound (5.97 g, 13.97 mmol, 46.79%). 1H NMR (400.0 MHz, DMSO) δ 12.72 (s, 1H), 9.03 (s, 1H), 8.46 (d, J=8.5 Hz, 2H), 8.23 (s, 1H), 8.01 (d, J=8.5 Hz, 2H), 3.49 (t, J=6.8 Hz, 1H) and 1.20 (d, J=6.8 Hz, 6H) ppm; MS (ES+) 428.0.
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