Acetic Acid → 6-Bromo-2-methoxy-3-methyl-3h-imidazo[4,5-b]pyridine
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:10])[C:5]([NH:8][CH3:9])=[N:6][CH:7]=1.[CH3:11][O:12][C:13](OC)(OC)OC.C(O)(=O)C>CCOC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]2[N:10]=[C:13]([O:12][CH3:11])[N:8]([CH3:9])[C:5]2=[N:6][CH:7]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 5-bromo-N*2*-methyl-pyridine-2,3-diamine (Stage 67.1.4, 960 mg, 4.75 mmol) and tetramethylorthocarbonate (Aldrich, Buchs, Switzerland, 2 ml, 14.7 mmol) and acetic acid (0.273 ml, 4.75 mmol) was stirred for 90 min at 100° C. The reaction mixture was diluted with EtOAc and washed with saturated aqueous NaHCO3 and brine. The aqueous layer was extracted with EtOAc and the combined organic layers washed with saturated aqueous NaHCO3 and with brine, then dried over Na2SO4, filtered and evaporated. The crude product was dry loaded on silica gel and purified by MPLC (DCM/MeOH 0%-4%) to give the title compound as a green solid. (HPLC: tR 2.83 min (Method A); M+H=242, 244 MS-ES).