6-Bromo-2-methylimidazo[1,2-a]pyrazine

To a well stirred solution of 6-bromo-2-methyl imidazo[1, 2-a]pyrazine (3 g, 14.15 mmol) in DMF (15 ml) was added N-lodoosuccinimide (3.82g, 16.98 mmol) and the reaction mixture was allowed to stir at 80C for 12 h under nitrogen. After complete consumption of the SM (Monitored by LCMS) the reaction mixture was diluted with ethyl acetate, washed successively with water and brine, dried over sodium sulphate and evaporated under reduced pressure to get the crude compound, which was purified by column chromatography (100-200 mesh silica gel, eluent; 20% ethyl acetate in hexane) to give the title compound as a yellowish solid [1.5 g, 31% (After two steps)]. LCMS rt 2.89 min MH* 338.1H NMR (400 MHz, DMSO-de) delta 8.74 (s, 1H), 8.49 (s, 1H), 2.44 (s, 3 H).2-amino-5-bromopyrazine (10g, 57m mol) and 1-bromo-2, 2-dimethoxy-propane (15 g) were dissolved in I PA (30 ml_) and heated at 100 C in a sealed tube for 3 days. The reaction was quenched with sodium bicarbonate solution and filtered and extracted with ethyl acetate; the organic layer was dried over sodium sulphate and concentrated to give a brown solid that was used for the next step without further purification.In a sealed tube, 4-bromo-2-ethoxybenzamide (288 mg, 0.1.18 mmol), 6-bromo-2- methylimidazo[l, 2-a]pyrazine (275 mg, 1.30 mmol), copper (I) iodide (22.5 mg, 0.118 mmol, 0.1 eq.), K3PO4 (526 mg, 2.48 mmol, 2.1 eq.) and 1, 10-phenantroline (42.5 mg, 0.236 mmol, 0.2 eq.) in dioxane (5 mL) was heated at 120C overnight. The reaction mixture was filtered on celite, concentrated under vacuo, and purification on column chromatography (S1O2, CH2C12 / MeOH 99/1 to 98/2) afforded 159 mg (36%) of the title product as a white solid. MS (m/e): 375.2 (M+H+, Br).

Molecular Weight:212.05
XLogP3:2.1
Hydrogen Bond Acceptor Count:2
Exact Mass:210.97451
Monoisotopic Mass:210.97451
Topological Polar Surface Area:30.2
Heavy Atom Count:11
Complexity:153
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes