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ChemicalBook CAS DataBase List 6,8-Dibromo-imidazo[1,2-a]pyrazine-2-carboxylic acid ethyl ester

6,8-Dibromo-imidazo[1,2-a]pyrazine-2-carboxylic acid ethyl ester synthesis

2synthesis methods
-

Yield:87597-21-5 79%

Reaction Conditions:

in 1,2-dimethoxyethane at 20 - 80; for 24 h;

Steps:

Ethyl 6,8-dibromoimidazo[l,2-a]pyrazine-2-carboxylate (Sl.l)

To a mixture of 2-amino-3,5-dibromopyrazine (3.0 g, 11.86 mmol) in anhydrous DME (12 mL) was added ethyl bromopyruvate (2 mL ~ 90% pure, 14.34 mmol) at r.t. The reaction mixture was heated at 80 °C for 24 hr. The mixture was then diluted with DCM, washed with sat. NaHC03 solution (x3), dried over MgSO4 and the solvent concentrated in vacuo. The resi- due was then triturated with cold diethyl ether and the solid was collected via filtration to give the title compound as a fawn color powder (3.26 g, 79%). This material was used in the next step without further purification. 1H NMR (400MHz, CDC13) d 8.29 (s, 1H), 8.25 (s, 1H), 4.49 (q, J = 7.1 Hz, 2H), 1.44 (t, J = 7.1 Hz, 3H). LCMS: (0 - 100 % Acetonitrile over 5 min, 0.1% formic acid throughout) Rf = 3.20 min, (ESI) m/z: 349.7 (M+H, 100%).

References:

WO2021/243421,2021,A1 Location in patent:Page/Page column 89; 110; 111