4-broMo-1-Methyl-1H-iMidazole-2-carbaldehyde synthesis

Yield: 40%

Reaction Conditions:

with N-Bromosuccinimide in N,N-dimethyl-formamide at 20; for 144 h;

Steps:

-Bromo-1 -methyl-1 H-imidazole-2-carbaldehydeA solution of 1 -methy-1 H-imidazole-2-carbaldehyde (10 g, 90 mmol) in deoxygenated DMF (300 mL) was treated with N-bromosuccinimide(17.8 g, 100 mmol) and the resulting solution stirred at RT for 6 days. Water (750 mL) was added and the resulting mixture was extracted with EtOAc (4 X 200 mL) the combined extracts were dried over Na₂SO₄, filtered and the volatiles removed in vacuo. The residue was purified by column chromatography on silica gel (n-heptane/EtOAc = 4/1 ) to yield the title compound (7.33 g, 40%) as a white solid. LC-MS: m/z = 191 .2 (MH⁺), t_R = 0.48 minutes, method A. ¹H NMR (600 MHz, DMSO-c/₆): δ 9.62 (s, 1 H), 7.80 (s, 1 H), 3.92 (s, 3H).

References:

H. LUNDBECK A/S;PÜSCHL, Ask;NIELSEN, Jacob;KEHLER, Jan;KILBURN, John, Paul;MARIGO, Mauro;LANGGÅRD, Morten WO2011/72694, 2011, A1 Location in patent:Page/Page column 42-43