Hydrochloric Acid → [5-Bromo-3-methyl-2-(3-trifluoromethoxy-phenyl)-3H-imidazol-4-yl]-methanol

HRID 545362Notes

Reaction equation

[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]

Participants

Conditions

Temperature: -70 °C

Procedure

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).

Workup

temperatureThe reaction mixture was warmed up to 0° C. and after 30 min
temperatureafter warming up to RT
extractionit was extracted twice with EtOAc
washthe organic phases were washed with water
dry with materialdried over magnesium sulfate
filtrationfiltered
customevaporated
customThe residue was purified by flash column chromatography (n-heptane/EtOAc 9:1 to 1:1)

Sources & evidence

ORD record: ord-fd150af9fa444993b6e1ee8216d261e6
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07935707B2

Reaction notes

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