Isopropanol → HCID 69099755, compound

To a solution of 3-bromo-furo[3,4-b]pyridine-5,7-dione (200 mg, 0.877 mmol) in THF (3 ml) at −10° C. was added Mg(ClO4)2 (235 mg, 1.053 mmol, 1.2 equiv.) and the reaction mixture was stirred for 5 min at that temperature. Then isopropanol (6 ml) was added and the reaction mixture was stirred at 25° C. for 16 hours. The volatilities were removed in vacuo and the resultant residue was dissolved in EtOAc (30 ml). The organic layer was washed with water (15 ml) and brine (15 ml), dried over anhydrous Na2SO4, filtered and evaporated off in vacuo. The crude material thus obtained was purified by column chromatography over normal silica gel (30-50% EtOAc/hexane) to afford 5-bromo-pyridine-2,3-dicarboxylic acid 2-isopropyl ester (210 mg, 83.1%) as light brown solid, MS: m/e=286.0 (M−H+).

1. stirringthe reaction mixture was stirred at 25° C. for 16 hours
2. customThe volatilities were removed in vacuo
3. dissolutionthe resultant residue was dissolved in EtOAc (30 ml)
4. washThe organic layer was washed with water (15 ml) and brine (15 ml)
5. dry with materialdried over anhydrous Na2SO4
6. filtrationfiltered
7. customevaporated off in vacuo
8. customThe crude material thus obtained
9. customwas purified by column chromatography over normal silica gel (30-50% EtOAc/hexane)

ORD record

ord-67d8772ed0ab47d6b2eefa4e564202fc

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08772300B2