(2-Chloro-4-methylphenyl)boronic acid → 2'-Chloro-4'-methyl-biphenyl-4-carboxylic acid {2-[(2-dimethylamino-ethyl)-methyl-amino]-benzothiazol-6-yl}-amide

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Reaction Steps

The title compound is prepared by following a procedure analogous to Example 113, Step 1, using N-{2-[(2-dimethylamino-ethyl)-methyl-amino]-benzothiazol-6-yl}-4-iodo-benzamide (0.40 g, 0.83 mmol) and 2-chloro-4-methyl-phenyl boronic acid (0.17 g, 0.10 mmol) to afford 2′-chloro-4′-methyl-biphenyl-4-carboxylic acid {2-[(2-dimethylamino-ethyl)-methyl-amino]-benzothiazol-6-yl}-amide (0.21 g, 0.44 mmol, 53%). The material is dissolved in EtOH, treated with 1.0 M HCl in EtOH (0.44 mL), concentrated and recrystallized from EtOH/Heptane to give 0.20 g (88%) as the hydrochloride salt. LC/MS, Retention time=5.04 min; (m/z): calcd for C26H27ClN4OS (M+H)+: 479.4; found: 479.0.

Provenance & Evidence