[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][C:8](Br)=[CH:7][C:5]=2[N:6]=1.CN(C)CCN(C)C.C([Li])(C)(C)C.[B:25](OC(C)C)([O:30]C(C)C)[O:26]C(C)C.S(=O)(=O)(O)O>C1COCC1.CCCCC>[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][C:8]([B:25]([OH:30])[OH:26])=[CH:7][C:5]=2[N:6]=1
A solution of Intermediate 63 (459.1 mg) in anhydrous THF (30 ml) was added with N,N,N′,N′-tetramethylethylenediamine (1.51 ml, WAKO), cooled to −78° C. under argon atmosphere, then added dropwise with 1.62 M solution of t-butyllithium in pentane (7.06 ml) and stirred for 30 minutes. The reaction mixture was added dropwise with (iPrO)3B (2.77 ml), stirred for 30 minutes, then warmed to room temperature and further stirred for 1.5 hours. The reaction mixture was added with 0.5 M aqueous sulfuric acid (7.5 mL) and extracted with diethyl ether (50 ml×3). The organic layer was washed with saturated brine and dried, and then the solvent was evaporated under reduced pressure to obtain crude 2-amino-5-benzothiazoleboronic acid. According to the procedure described in the synthesis method of Compound of Example 001 (Preparation Method 4, Step d-1) with the modifications that the reaction was carried out for 12 hours, and the purification was performed by flash column chromatography (hexane:ethyl acetate=2:1), the above compound was reacted with Intermediate 3 (344 mg), 2 M aqueous sodium carbonate (4.5 ml) and (Ph3P)4Pd (179 mg) and treated to obtain the title compound (Compound No. 284, 76 mg).
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