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tert-butyl 2-bromo-1-methyl-1H-imidazole-4-carboxylate[ No CAS ]
[ 852181-03-4 ]
Yield
Reaction Conditions
Operation in experiment
100%
With trifluoroacetic acid; In dichloromethane; at 20.0℃; for 12.0h;
At room temperature, 645 mg (2.47 mmol) oftert-butyl 2-bromo- 1-methyl-i H-imidazole-4-carboxylatewere stirred in a mixture of 1.7 g of trifluoroacetic acid andml of dichloromethane for 12 hours. The solvent wasremoved. The evaporation residue obtained consisted to95% of the target product 2-bromo-i -methyl-1H-imidazole4-carboxylic acid, which corresponds to a virtually quantitative yield.log P[a]: 0.0; 1H-NMR (CD3CN, 400 MHz); delta = 3.65 (s, 3H),7.78 (s, 1H) ppm.
With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; toluene; for 4.0h;
0.32 ml of oxalyl chloride (1.2 eq.) were added dropwise to a solution of 681 mg (3.32 mmol) of 2-bromo- i-methyl-1H-imidazole-4-carboxylic acid in 7 ml of dichloromethane and 3 drops of dimethylformamide. Afier 4 hours, the mixture was evaporated to dryness. 10 ml of dichloromethane, 359 mg (1 eq.) of N-methylpyridine-3- amine and 6 eq. of N,N-diisopropylethylamine were added to the residue and the mixture was then stirred for one hour. The mixture was then evaporated to dryness and the residue was chromatographed by MPLC on silica gel using the mobile phase ethyl acetate/methanol. Yield 411 mg (43% of theory). log P[n]: 0.76; 1H-NMR (CD3CN, 400 MHz); delta=3.41 (s, 3H);3.51 (s, 3H), 7.28-7.35 (m, 2H), 7.59-7.61 (m, 1H), 8.37-8.43 (m, 2H) ppm.
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