N-Iodosuccinimide → 4-Iodo-2-(thieno[2,3-d]pyridazin-3-yl)furo[2,3-c]pyridin-7-amine
Reaction equation
[S:1]1[C:5]2=[CH:6][N:7]=[N:8][CH:9]=[C:4]2[C:3]([C:10]2[O:19][C:13]3=[C:14]([NH2:18])[N:15]=[CH:16][CH:17]=[C:12]3[CH:11]=2)=[CH:2]1.[I:20]N1C(=O)CCC1=O>CN(C)C=O>[I:20][C:17]1[CH:16]=[N:15][C:14]([NH2:18])=[C:13]2[O:19][C:10]([C:3]3[C:4]4[C:5](=[CH:6][N:7]=[N:8][CH:9]=4)[S:1][CH:2]=3)=[CH:11][C:12]=12Participants
4
Procedure
A solution of 2-(thieno[2,3-d]pyridazin-3-yl)furo[2,3-c]pyridin-7-amine (30.0 mg, 0.112 mmol) and N-iodosuccinimide (101.6 mg, 0.4516 mmol) in N,N-dimethylformamide (2 mL) was stirred at 40° C. for 45 min. The reaction was removed from the heat and 1.0 M aqueous sodium thiosulfate solution (2 mL) was added. The crude mixture was concentrated in vacuo. The residue was then suspended in water and the fine solid was filtered off and dried, giving 39.0 mg (88%) of the title compound as a brown solid. 1H NMR (400 MHz, DMSO-d6): δ 10.48 (d, J=1.52 Hz, 1H), 10.02 (d, J=1.52 Hz, 1H), 9.04 (s, 1H), 7.96 (s, 1H), 7.45 (s, 1H), 6.89 (s, 2H); MS (ESI): 395.07 [M+H]+; HPLC: tR=2.83 min.