[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9]([C:11]1[N:12]([CH3:28])[C:13]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([O:23][C:24]([F:27])([F:26])[F:25])[CH:18]=2)=[N:14][C:15]=1[Br:16])=O.CCOC(C)=O.Cl>C1COCC1.O>[Br:16][C:15]1[N:14]=[C:13]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([O:23][C:24]([F:27])([F:26])[F:25])[CH:18]=2)[N:12]([CH3:28])[C:11]=1[CH2:9][OH:8]
A solution of 5.62 ml (5.6 mmol) of lithium aluminium hydride (1 molar in THF) was slowly added to a solution of 3.55 g (9.4 mmol) of 5-bromo-3-methyl-2-(3-trifluoromethoxy-phenyl)-3H-imidazole-4-carboxylic acid methyl ester in 100 ml of THF cooled down to −70° C. The reaction mixture was warmed up to 0° C. and after 30 min cooled down to −50° C. and hydrolyzed with i) EtOAc, ii) H2O and iii) HCl (1N); after warming up to RT, it was extracted twice with EtOAc; the organic phases were washed with water, dried over magnesium sulfate, filtered and evaporated. The residue was purified by flash column chromatography (n-heptane/EtOAc 9:1 to 1:1) to give 3.25 g (99%) of the title compound as colorless solid. MS: 351.0 (MH+, 1Br).
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