(5-Bromo-thiophen-3-yl)-(4,4-dimethyl-azepan-1-yl)-methanone (0.31 g, 0.99 mmol), together with caesium carbonate (0.483 g, 1.49 mmol), [4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyrazol-1-yl]-acetic acid ethyl ester (0.28 g, 1.0 mmol) and palladium tetrakis(triphenylphosphine) (114 mg, 0.1 mmol) were taken up in DME (9 mL), IMS (2 mL) and water (1 mL) and the vessel was purged with argon. The reaction mixture was heated by microwave irradiation to 140° C. for 20 minutes and then diluted with water then treated with dilute HCl (pH adjusted to 4) and extracted with DCM (×3). The organic solution was dried over sodium sulfate, filtered and the solvent evaporated. The residue was purified by chromatography on a silica II cartridge, eluting with 50 then 100% ethyl acetate in cyclohexane then 5% acetic acid in ethyl acetate. The residue was further purified by HPLC, eluting with 10%-98% acetonitrile in water (0.1% formic acid) and the fractions containing desired product were freeze-dried to give the title compound (0.015 g). LCMS m/z 362.24 [M+H]+ R.T.=8.84 min (Analytical Method 2).
