4,5-DIHYDRO-4-OXOFURO[3,2-C]PYRIDINE

Reference Example 3 furo[3, 2-c]pyridin-4(5H)-one; (2E)-3-(2-Furyl)acryloyl azide (150 g, 920 mmol) was added to toluene (800 mL) heated to 100°C, and the mixture was stirred for 30 min. The solvent was evaporated under reduced pressure. The residue was dissolved in orthodichlorobenzene (800 mL), and iodine (1 g) was added. The mixture was stirred at 180°C for 2 hr, and the solvent was evaporated under reduced pressure. The residue was dissolved in methanol, the precipitate was filtered off, and the filtrate was concentrated under reduced pressure. The residue was washed with diisopropyl ether to give the title compound (100 g, yield 80percent). (E)-3-(Furan-2-yl)acryloyl azide (Example 221 A, 0.501 g, 3.071 mmol) was dissolved in toluene (5 mL) and heated at reflux for 40 min. The mixture was then concentrated to afford a dark brown oil which was then dissolved in o-dichlorobenzene (9 mL) and iodine (8 mgs, 0.0315 mmol) was added. The reaction mixture was stirred for 2 hours at 180 °C. The mixture was cooled down to rt and ethyl acetate was added. The resulting precipitate was filtered. The filtrate was evaporated and the residue was dissolved in ethyl ether (10 mL) and extracted with 0.5M aq. sodium hydroxide (2 x 10 mL). The aqueous phase was acidified with 1.5N aq. HCl until the pH reaches 1.0. The acidified aqueous phase was then extracted with ethyl acetate (3x) and the combined organic extracts were dried over anhydrous sodium sulfate, filtered and concentrated. The resulting red-brown solid was triturated in cold ethyl ether twice to give the title material (0.249g, 60percent) as a red-brown solid. LC (Method A): 0.883 min. A mixture of (E) -3- (furan-2-yl) acryloyl azide (10 g 61.3 mmol) in toluene (100 mL) was stirred at 100 for 30 min. The solvent was evaporated. The residue was dissolved in 1 2-dichlorobenzene (90 g 613 mmol) and iodine (0.062 g 0.245 mmol) . The mixture was stirred at 180 for 2 h. The solvent was evaporated. The residue was dissolved in MeOH (200 mL) . The precipitate was filtered off and the filtrate was concentrated and washed with TBME (50 mL) to give furo [3 2-c] pyridin-4 (5H) -one (5 g 31.5 mmol 51.3 yield)

Molecular Weight:135.12
XLogP3:0.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:135.032028402
Monoisotopic Mass:135.032028402
Topological Polar Surface Area:42.2
Heavy Atom Count:10
Complexity:188
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes