2-CHLORO-5-BORONOBENZAMIDE synthesis

Yield:1143020-40-9 39%

Reaction Conditions:

copper(l) iodide in methanol at 65; for 18 h;

Steps:

41

Intermediate 41: 2-Chloro-5-(lH-imidazol-l-yl)benzamide; Copper(I) iodide (9.55 mg, 0.05 mmol) was added to 2-chloro-5-boronobenzamide (0.20 g, 1.00 mmol) and imidazole (82 mg, 1.20 mmol) in MeOH (4 mL) and the solution was heated at 65 ⁰C for 18 hours. The reaction mixture was concentrated in vacuo and the residue was purified by chromatography on silica gel eluting with MeOH/DCM (0 - 10%) to give the title compound as a colourless solid (86 mg, 39%): ¹H NMR 57.18 (IH, t), 7.68 - 7.71 (IH, m), 7.75 (IH, s), 7.77 - 7.81 (IH, m), 7.84 (IH, d), 7.88 (IH, t), 8.00 (IH, s), 8.39 (IH, s); MS 222.

References:

WO2009/47558,2009,A1 Location in patent:Page/Page column 39; 148