ChemicalBook CAS DataBase List 5-BROMO-1H-PYRROLO[2 , 3-B]PYRIDIN-2(3H)-ONE

5-BROMO-1H-PYRROLO[2 , 3-B]PYRIDIN-2(3H)-ONE synthesis

6synthesis methods

Product Name:5-BROMO-1H-PYRROLO[2 , 3-B]PYRIDIN-2(3H)-ONE
CAS Number:183208-34-6
Molecular formula:C7H5BrN2O
Molecular Weight:213.03

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5-BROMO-1H-PYRROLO[2 , 3-B]PYRIDIN-2(3H)-ONE

183208-34-6
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Yield:183208-34-6 71%

Reaction Conditions:

with ammonium chloride;zinc in tetrahydrofuran;water at 20; for 0.333333 h;

Steps:

b b) 5-Bromo-7-azaoxindole
b) 5-Bromo-7-azaoxindole A solution of 3,3,5-tribromooxindole (5.0 g, 13.4 mmol) in fresh THF (100 ML) is stirred at room temperature and a saturated aqueous solution of ammonium chloride (100 ML) is added.. The flask is placed in a water bath and activated zinc dust (15.0 g, 230 mmol) is added.. The mixture is stirred for 20 min and the zinc is removed by filtration through a pad of diatomaceous earth.. The organic layer is separated and the aqueous layer is extracted with THF (20 ML).. The combined organic layers were washed with saturated brine solution, dried over anhydrous magnesium sulfate and the solvent removed under reduced pressure.. The brown residue is triturated with water (20 ML) and the tan solid is collected by filtration and dried under vacuum to give 5-bromo-7-azaoxindole as a tan solid, 2.02 g (71%). 1H NMR (DMSO-d6) δ 11.13 (s, 1H), 8.15 (s, 1H), 8.76 (s, 1H), 3.57 (s, 2H). MS (AP-ve) 211 (100) (M-H).

References:

Glaxo Wellcome Inc. US6350747, 2002, B1 Location in patent:Page column 69

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