2-Bromo-4-methylimidazole

While a mixture of 23.9 g (100.0 mmol) of 2, 4-dibromo-5-methylimidazole, 29.4 g (300.0 mmol) of cyclohexanone, and 23.9 g (259.4 mmol) of toluene was stirred at ordinary temperature, 22.5 g (150.0 mmol) of sodium iodide was added thereto to prepare a reaction liquid. After the reaction liquid was stirred at 105°C for 12 hours under a nitrogen stream, the liquid was stirred under ice cooling for 1 hour. When 2-bromo-4-methylimidazole in the reaction liquid was analyzed by means of HPLC, it was confirmed that the product was formed in an amount of 13.7 g (82.3 mmol, conversion: 85.3percent). After the reaction liquid was concentrated under reduced pressure, the product was purified by silica gel chromatography (ethyl acetate/hexane system) and, after volatile matter was further vaporized to solidify the product, crystals of 2-bromo-4-methylimidazole were obtained in an amount of 12.6 g (yield: 78.1percent) as a residue. Incidentally, the NMR spectrum of the crystals was measured and was compared with the NMR spectrum of its specimen, whereby it was confirmed that the product is 2-bromo-4-methylimidazole.To a microwave vial were added the product of Example 126A (0.025 g, 0.049 mmol), 2- bromo-4-methyl-l //-imidazole (0.016 g, 0.098 mmol), potassium carbonate (0.020 g, 0.15 mmol), and [(l, 3, 5, 7-tetramethyl-6-phenyl-2, 4, 6-trioxa-6-phosphaadamantane)-2-(2'-amino-l, T- biphenyl)]palladium(II) methanesulfonate (meCgPPh Pd G3, 3.23 mg, 4.88 pmol). The vial was sealed, evacuated, and refilled with nitrogen. The evacuation/refill cycle was repeated three additional times. Next, a mixture of 1, 4-dioxane (0.20 mL) and water (0.049 mL)- which had been degassed using the same evacuation/refill process described above- was added. The vial was then heated to 125 C for 5 hours. The vial was cooled to ambient temperature. Next, acetonitrile (2 mL) was added, followed by 1 M hydrochloric acid (6 mL). The resulting mixture was stirred for 5 minutes, and then the precipitate was collected by filtration. The solid was washed with acetonitrile (2 mL) and ethyl acetate (2 mL) and then dried to give the title compound (0.017 g, 0.034 mmol, 69% yield). JH NMR (500 MHz, DMSO-de) d ppm 14.56 (br s, 2H), 8.68 (d, / = 1.6 Hz, 1H), 8.11 - 8.03 (m, 2H), 7.59 - 7.53 (m, 3H), 7.48 (s, 1H), 7.40 - 7.36 (m, 2H), 7.34 - 7.29 (m, 1H), 5.32 (s, 2H), 4.20 (s, 2H), 2.37 (s, 3H); MS (APCI+) m/z 467.3 [M+H]+.

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