4-Methyl-5-bromoimidazole

Tert-butyl 5-(2-fluoro-3-nitrophenyl)-4-methyl-1H-imidazole-1-carboxylate (51b) To a mixture of General procedure: A mixture of 4-methyl-3-(4-(pyridin-2-ylmethoxy)benzamido)phenyl boronic acid (50 mg, 0.14 mmol), Cs2CO3 (135 mg, 0.41 mmol), Pd(PPh3)4(23.93 mg, 0.02 mmol) and 4-bromo-1H-imidazole (26 mg, 0.18 mmol) was purged with nitrogen before adding degassed dioxane (690 muL) and water (230 muL) and heating in a microwave for 40 min at 150 C. After cooling, the aqueous layer was removed with a pipette, and the organic layer was diluted with DMSO (1 mL) and filtered through a 0.2 mum filter. The filtrate was concentrated to a volume of 1 mL and purified by Gilson HPLC (20-75% MeCN/10 mM NH4OAc in water). The fractions were concentrated and lyophilized to yield the product (19 mg, 0.049 mmol, 35%). 1H NMR (DMSO-d6) delta ppm 12.11 (s, 1H), 9.76 (s, 1H), 8.59 (d, 1H), 7.97 (d, 2H), 7.85 (td, 1H), 7.70 (s, 1H), 7.67 (s, 1H), 7.56 (m, 2H), 7.36 (dd, 1H), 7.21 (d, 1H), 7.15 (d, 2H), 5.27 (s, 2H), 2.18 (s, 3H). LCMS (M+H) = 385.PREPARATION 705-Bromo-1 , 4-dimethyl-1 H-imidazole To a cooled (0 C) suspension of sodium hydride (60% wt / wt in mineral oil, 149 mg, 3.73 mmol, 1.2 eq.) in anhydrous tetrahydrofuran (10 ml_), under an atmosphere of nitrogen, was added a solution of 5-bromo-4-methyl-1 H-imidazole (500 mg, 3.11 mmol) in tetrahydrofuran (5 ml_). The resulting mixture was stirred at room temperature for 30 min before adding methyl iodide (661 mg, 4.66 mmol, 1.5 eq.). The reaction mixture was stirred for 30 min before partitioning between ethyl acetate (100 ml_) and water (20 ml_). The organic phase was dried over magnesium sulphate and the resulting mixture filtered. The filtrate was evaporated under reduced pressure and the resulting residue purified by chromatography on silica gel (40 g) eluting with a gradient of methanol in dichloromethane (0:100 to 5:95) to give the title compound as a clear oil (80 mg, 15%). 1H NMR (400 MHz, CDCI3): delta = 2.10 (s, 3H), 3.59 (s, 3H), 7.53 (s, 1 H)MS: APCI+ m /z = 174, 176 [MH+]To a suspension of NaH (2.78g, 60% 69 mmol) in tetrahydrofuran (100 ml) at 0 0C is slowly added a solution of 3-bromo-4-methylimidazole (10.0g, 62 mmol) in dry tetrahydrofuran (100 ml) over 20 minutes. The mixture is stirred at room temperature for 1 hour. 2-(Trimethylsilyl)ethoxymethyl chloride (11 ml, 62 mmol) is then added at 0 0C and the mixture is stirred at room temperature for 2 hours. The reaction mixture is diluted with ethyl acetate (600 ml), washed with water (80 ml), brine (80 ml), dried over Na2SO4, filtered, and concentrated in vacuo to give a yellow oil. LC-MS the product is obtained as a -1:1 mixture of regioisomers 38g, 91%, LC/MS ESI m/z (M+H)+ = 291.4.EXAMPLE 6 Using a procedure similar to that described in Example 1, 13 g of methyl isocyanate were added dropwise to 40 g of

Molecular Weight:161.00
XLogP3:1.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Exact Mass:159.96361
Monoisotopic Mass:159.96361
Topological Polar Surface Area:28.7
Heavy Atom Count:7
Complexity:66.7
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes