6-BROMO-4-METHYL-1H-BENZOIMIDAZOLE

(Bromomethyl) cyclopropane (3.75 mmol, 0.36 mL) was added drop-wise to mixture of 6-bromo-4-methyl-lH- benzo [d] imidazole (2.5 mmol) and potassium carbonate (3.75 mmol, 0.52 g, ) in DMF (8 mL). The mixture was stirred at room temperature for 48 hours and 60°C for 3 h. The mixture was diluted with ethyl acetate and water and the organic extract was washed with brine, dried (MgS04) and concentrated under reduced pressure. Purification of the crude product by column chromatography (silica gel, gradient of 30-100percent ethyl acetate in isohexane) gave the title compound (containing ~25percent of the isomeric 5-bromo- 1- (cyclopropylmethyl) -7-methyl-lH-benzo [d] imidazole) as an off-white solid (0.29 g, 44percent).A mixture of 5-bromo-3-methylbenzene-l , 2-diamine (2.5 mmol, 0.5 g) , was suspended in trimethylorthoformate (1042) (34 mL) and para-toluene sulfonic acid monohydrate (0.17 g) was added. The suspension was heated at 115 °C for 1.5 hours, and then cooled to room temperature. The mixture was diluted with dichloromethane and washed with (1043) saturated sodium bicarbonate solution and brine. The organic extracts were combined, passed through a phase separator cartridge and concentrated under reduced pressure to afford the crude title compound as a brown solid (0.78 g, >100percent) which was used without further purification.6-Bromo-4-methyl-lH-benzo[d]imidazole (1.02 g, 4.83 mmol) was dissolved in tetrahydrofuran (10 mL) at room temperature with stirring under nitrogen. 3, 4-Dihydro-2H-pyran (3.5 mL, 38.4 mmol) and methanesulfonic acid (0.032 mL, 0.48 mmol) were added and the resulting mixture heated at 75 0C for 49 h. The resulting mixture was cooled to room temperature, diluted with ethyl acetate and washed with saturated aqueous sodium bicarbonate and brine. The organics were dried over magnesium sulfate, filtered and concentrated under reduced pressure. Flash chromatography (50-100 percent ethyl acetate in hexanes) gave the desired product (1.32 g, 4.47 mmol, 93 percent yield) as a light yellow solid. MS (ESI) m/z 295.1 [M] +, 297.3 [M+2]+.

Molecular Weight:211.06
XLogP3:2.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Exact Mass:209.97926
Monoisotopic Mass:209.97926
Topological Polar Surface Area:28.7
Heavy Atom Count:11
Complexity:151
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes