[Br:1][C:2]1[CH:3]=[C:4]([NH2:12])[C:5]2[CH:6]=[N:7][N:8]([CH3:11])[C:9]=2[CH:10]=1.N1C=CC=CC=1.Cl[CH2:20][C:21]1[N:22]=[C:23]([C:26]([Cl:28])=O)[S:24][CH:25]=1.C(=O)(O)[O-:30].[Na+]>C(Cl)Cl.O>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[CH3:11])=[C:4]([NH:12][C:20]([C:21]2[N:22]=[C:23]([CH2:26][Cl:28])[S:24][CH:25]=2)=[O:30])[CH:3]=1
6-Bromo-1-methyl-1H-indazol-4-amine (1 g, 4.42 mmol) was dissolved in DCM (DCM) (10 ml) and pyridine (0.429 ml, 5.31 mmol) added. The mixture was cooled to 0° C. in an ice-water bath and 4-(chloromethyl)-1,3-thiazole-2-carbonyl chloride (0.867 g, 4.42 mmol) in DCM (10 ml) was added portionwise over 5 mins. The mixture was stirred for 2 hours and allowed to warm to room temperature. Saturated sodium bicarbonate solution (15 ml) was added and the mixture stirred vigorously for 10 mins. The mixture was diluted with water (50 ml) and DCM (50 ml), but a precipitate was still present. This was collected by filtration, washed with DCM and air dried to afford the title compound as a yellow/brown solid (860 mg).
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