DIMETHYL 5-BROMOPYRIDINE-2,3-DICARBOXYLATE

2-Bromo-7-(4-fluoro-benzyl)-5, 9-dihydroxy-pyrrolo[3, 4-g]quinoline-6, 8-dione 1008 Following the literature procedure of M.-D. Le Bas et al. (Synthesis 2001, 16, p. 2495), 100 ml CClTo a mixture of 3-bromoquinoline (10 ml, 72.7 mmol) and water (20OmL) was added KMnOCompound B-2: 5-Bromo-pyridine-2, 3-dicarboxylic acid 2-Bromo-7-(4-fluoro-benzyl)-5, 9-dihydroxy-pyrrolo[3, 4-g]quinoline-6, 8-dione 1008 Following the literature procedure of M.-D. Le Bas et al. (Synthesis 2001, 16, p. 2495), 100 ml CClTo a mixture of 3-bromoquinoline (10 ml, 72.7 mmol) and water (20OmL) was added KMnOCompound B-2: 5-Bromo-pyridine-2, 3-dicarboxylic acid 2-Bromo-7-(4-fluoro-benzyl)-5, 9-dihydroxy-pyrrolo[3, 4-g]quinoline-6, 8-dione 1008 Following the literature procedure of M.-D. Le Bas et al. (Synthesis 2001, 16, p. 2495), 100 ml CCl4 was mixed with 250 ml of an aqueous NaOCl solution. To this mixture was added 40 mg of RuO2, followed by 3 g 3-bromoquinoline dissolved in 50 ml CCl4. Additional 30 ml portions of bleach were added at 2, 4, and 6 h. After 24 h, the aqueous layer was collected and acidified to pH 1 with 3N HCl. The aqueous layer was then extracted with ethyl acetate, dried over Na2SO4 and volatiles removed by evaporation to give the 1.7 g product as a yellow resin, (48% yield). 1H NMR and MS data matched that reported in the literature. The resulting anhydride, 1 g, was then carried through the previously reported multistep sequence to afford the corresponding cyano-ester. Dieckmann condensation between 80 mg (0.3 mmol) of the ester and 80 mg (3.6 mmol) of the imide utilizing 900 uL LiHMDS in 2 ml dry THF gave the crude product. After the typical work-up, approximately 60 mg (30%) of unpurified product was obtained as a yellow solid which was further refined by trituration with diethyl ether to provide 2 mg highly pure product 1008. 1H NMR (300 MHz, d6-DMSO) delta 9.20 (d, 1H), 9.05 (d, 1H) and 4.85 (s, 2H) ppm, MS=416.1 (M+H).To a mixture of 3-bromoquinoline (10 ml, 72.7 mmol) and water (20OmL) was added KMnO4 (69.0 g, 436 mmol) at 6 portion each 15 min at 80C with stirring. After allowing the reaction to cool to rt, MeOH (20 mL) was added to the solution. The resulting mixture was washed with toluene (100 mL)5 and the aqueous layer was adjusted to pH 1 with cone. HCl. The mixture was extracted twice with EtOAc/THF (10OmL / 50 mL). The combined extracts were washed with brine, dried over Na2SO4, and the solvent was removed in vacuo. Water was added to the residue, the resulting insoluble materials were filtered off. Isobutyl acetate was added to the filtrate, and then water was removed in vacuo. The resulting precipitates were collected by filtration, and dried to give 4.45 g of compound B-2 (yield = 25 %) as a colorless crystal. EPO

Molecular Weight:246.01
XLogP3:0.9
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:2
Exact Mass:244.93237
Monoisotopic Mass:244.93237
Topological Polar Surface Area:87.5
Heavy Atom Count:13
Complexity:233
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes