Methanol → Methyl 3-(bromoacetyl)benzoate

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3-{2-[5-(Adamantan-1-yloxymethyl)-2-cyclohexyl-1H-imidazol-4-yl]-thiazol-4-yl}-benzoic acid methyl ester. 3-(2-Bromo-acetyl)-benzoic acid methyl ester was prepared as described by Schmied (Schmied, Gading, Monatshefte Chem. 1953, 84, 491). A solution of this bromoketone (0.44 g, 1.7 mmol) and the thioamide from step c (0.52 g, 1.4 mmol) in methanol (10 ml) was heated under reflux for 5 h. The solvent was evaporated and the residue taken up in ethyl acetate and washed with saturated aqueous sodium hydrogen carbonate (2×20 ml), brine (20 ml) then dried (MgSO4). The crude product was purified by flash chromatography (Silica, DCM/ethyl acetate 95:5-90:10). Yield 0.36 g (48%). 1H NMR (300 MHz, CDCl3) 9.25 (1H, br s), 8.64 (1H, s), 8.16 (1H, d), 8.01 (1H, d), 7.51 (2H, m), 5.17 (2H, s), 3.95 (3H, s), 2.79 (1H, m), 2.20 (3H, br s), 2.07 (2H, m), 1.90-1.36 (20H, m).

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