7-Bromofuro[3,2-c]pyridin-4(5H)-one

To a mixture of furo [3 2-c] pyridin-4 (5H) -one (5 g 37.0 mmol) in MeCN (50 mL) was added a solution of NBS (8.56 g 48.1 mmol) in MeCN at 0 over 10 min. The resulting suspension was stirred at 0 for 1 h and warmed to rt for 10 min. Water (250 mL) and saturated aqueous NaHCO4. 7-Dibromofuror3, 2-clperidine; Combine 7-bromo-5H-furo [3, 2-c] pyridin-4-one (16.16 g, 75.5 mmol), dichloroethane (160 mL), and phosphorus oxybromide (100 g, 348.8 mmol) and heat at reflux for about 2 hours. Cool to room temperature and pour the reaction mixture into ice water (1 L). Adjust the pH to 8 with 5N NaOH, extract into dichloromethane, wash with brine, dry over magnesium sulfate, filter, and concentrate. Purification by flash chromatography, eluting with hexane: ethyl acetate gives the title compound as a white solid. HRMS : 274.8581 (M+).To a mixture of furo [3 2-c] pyridin-4 (5H) -one (5 g 37.0 mmol) in MeCN (50 mL) was added a solution of NBS (8.56 g 48.1 mmol) in MeCN at 0 over 10 min. The resulting suspension was stirred at 0 for 1 h and warmed to rt for 10 min. Water (250 mL) and saturated aqueous NaHCO3(10 mL) ware added to the mixture. Off-white solids ware collected by filtration and dried to afford 7-bromofuro [3 2-c] pyridin-4 (5H) -one (1.5 g 5.96 mmol 16.10 yield) 1HNMR(400 MHz CD3OD) delta 7.82 (d J 2.0 Hz 1H) 7.51 (s 1H) 7.05 (d J 2.4 Hz 1H) ES-LCMS m/z 214.0 215.9 (M+H)Preparation 20; 7-Bromofuro [3, 2-c] pyridine; 7-Bromo-5H-furoF3, 2-clpyn; Add N-bromosuccinimide (63.16 g, 354.9 mmol) as a solution in anhydrous acetonitrile (480 mL) to a suspension of 5H-furo [3, 2-c] pyridin-4-one (36.9 g, 273 mmol) in anhydrous acetonitrile (740 mL) at 0 C over 1 hour. Warm to room temperature, add anhydrous methyl alcohol (1.5 L) and stir at room temperature for 18 hours. Quench with water (20 ml) and saturated sodium bicarbonate (20 mL), concentrate to a volume of 1.3 liters, and pour into water (1.3 L). Collection of the precipitate by filtration and drying (vacuum oven 2 days 40-60 C) gives the title compound as an off-white solid. ESMS: (m/z) = 213.9, 215.9 (M++1).To a mixture of 7-bromofuro [3 2-c] pyridin-4 (5H) -one (250 mg 1.168 mmol) in 1 4-dioxane (12 mL) and water (4 mL) was added 1- (2-fluoro-4- (4 4 5 5-tetramethyl-1 3 2-dioxaborolan-2-yl) phenyl) -3- (4- ( (3-methyloxetan-3-yl) oxy) -3- (trifluoromethyl) phenyl) urea (656 mg 1.285 mmol) PdCl2(dppf) (85 mg 0.117 mmol) and Cs2CO3(761 mg 2.336 mmol) . The mixture was stirred at 110 for 30 min under a N2atmosphere under microwave. The residue was purified by preparative HPLC (MeCN/H2O as eluants acidic condition) to yield a white solid of 1- (2-fluoro-4- (4-oxo-4 5-dihydrofuro [3 2-c] pyridin-7-yl) phenyl) -3- (4- ( (3-methyloxetan-3-yl) oxy) -3- (trifluoromethyl) phenyl) urea (48.18 mg 0.089 mmol 7.63 yield) 1HNMR(400 MHz CD3OD) delta 8.20 (t J 8.4 Hz 1H) 7.85 (d J 2.0 Hz 1H) 7.80 (d J 2.4 Hz 1H) 7.61-7.51 (m 4H) 7.07 (d J 2.0 Hz 1H) 6.62 (d J 8.8 Hz 1H) 4.89 (d J 6.8 Hz 2H) 4.63 (d J 7.2 Hz 2H) 1.72 (s 3H) ES-LCMS m/z 518.0 (M+H)To a suspension of 227.1 7-Bromo-5-(2-(quinolin-2-yl)ethyl)furo[3, 2-c]pyridin-4(5H)-one DIAD (4.91 mmol, 992 mg) was added dropwise to PPh3 (753 mg, 2.80 mmol) in 20 mL of THF. The mixture was stirred for 30 min. Then

Molecular Weight:214.02
XLogP3:0.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:212.94254
Monoisotopic Mass:212.94254
Topological Polar Surface Area:42.2
Heavy Atom Count:11
Complexity:227
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes