5-(4-broMophenyl)pyrrolidin-2-one

To a solution of tert-butyl 2- ((1H-pyrrolo [2, 3-b] pyridin-5-yl) oxy)-4-(4, 4, 5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) benzoate (2.2 g, 5.00 mmol) in 1, 4-dioxane (50 mL) was added 5- (4-bromophenyl) pyrrolidin-2-one (1.2 g, 5.00 mmol), Pd (dppf) Cl 2 (183 mg, 0.25 mmol) and 1 N K 2CO 3 (15 mL), the mixture was stirred in a 80C oil bath under N 2 for about 18h. Cooled to r.t, extracted with DCM (50 mL2). The combined organic layers were concentrated and purified by column chromatograph on silica gel (100-200 mesh, eluent: MeOH: DCM= 1: 10) to give the crude product as brown solid. (2.4 g). [M+1] + 469.8.To a solution of methyl-4- (4-bromophenyl)-4-(hydroxyimino) butanoate (11.2 g, 39.16 mmol) in CH 3OH (100 mL) was added Zn (powder, 5.2 g, 78.32 mmol), the mixture was stirred in a 80C oil bath under N 2 for about 16h. Cooled to ambient temperature, filtered, the filtrate was concentrated. The residue was partitioned between DCM (500 mL) and Sat. NaHCO 3 (300 mL). The organic layer was separated, concentrated to give the crude product, which was slurry with PE (100 mL) to give the product as white solid. (6.5 g, 69.4%). [M+1] + 240.0, 241.9.

Molecular Weight:240.10
XLogP3:1.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:238.99458
Monoisotopic Mass:238.99458
Topological Polar Surface Area:29.1
Heavy Atom Count:13
Complexity:199
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes