4-chloro-1H-pyrrolo[2,3-b]pyridin-2(3H)-one

To a solution of 3, 3 -dibromo-4-chloro- 1H-pyrrolo [2, 3-bj pyridin-2(3B)-one(350 mg, 1.072 mmol) in MeOH (5 mL) was added acetic acid (5 mL) then zinc dust(351 mg, 5.36 mmol) in portions. The mixture was stirred at room temperature forlh. The reaction mixture was diluted with ethyl acetate (50 mL), filtered throughdiatomaceous earth and the filtrate neutralized with 10percent aq. NaHCO3 solution. Theorganic layer was separated out, dried over Na2SO4, filtered, and concentrated to afford a brownish solid. The solid was washed with hexane (2 x 20 mL) to afford 4- chloro-1H-pyrrolo[2, 3-bjpyridin-2(3B)-one (164 mg, 0.973 mmol, 91percent yield) as an off white solid. LCMS (ESI) m/e 168.9 [(M+H), calcd for C7H6C1N2O, 169.01;LC/MS retention time (method B): tR = 0.58 mm.ID. 4-Chloro-l .3-dihvdro-pyrrolo[2.3-61pyridin-2-oneA suspension of 3 , 3 -dibromo-4-chloro- 1 , 3 -dihydro-pyrrolo [2, 3 -]pyridin-2-one (1.05 g, 3.15 mmol), ethanol (120 mL) and 10percent Pd/C (391 mg) was hydrogenated at room temperature and room pressure for 6h 15 min. The reaction mixture was filtered through a pad of celite and washed with methanol. The solvents were 1 OD. 4-Chloro-l .3-dihydro-pyrrolo[2, 3-A mixture of 3, 3-dibromo-4-chloro-1, 3-dihydro-pyrrolo[2, 3-b]pyridin-2-one (0.745 g, 2.3 mmol), zinc dust (1.49 g, 23 mmol), acetic acid (10 mL) and methanol (10 mL) was stirred at room temperature for 2 hours. Compound 51 (3.6g) was dissolved in alcohol(50ml), to which acetic acid (2.0ml) wasadded slowly. The reaction was heated to reflux till completion. Filtration of the reaction mixturewas employed to remove the solid and the filtrate was concentrated in vacuum to give compound52 (1.12g).

Molecular Weight:168.58
XLogP3:0.7
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:168.0090405
Monoisotopic Mass:168.0090405
Topological Polar Surface Area:42
Heavy Atom Count:11
Complexity:185
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes