3-Fluoro-4-pyridinol

General procedure: In a typical reaction, 10 molpercent CuSO4·5H2O, (0.049 g, 0.2 mmol)and 6.7 molpercent EA (20 mg) were mixed in methanol followed by2 mmol of phenylboronic acid. This reaction mixture was kept ina preheated oil bath by maintaining the temperature at 60 °C andstirred under atmospheric pressure. After completion of the reac-tion, modified by TLC, the mixture was washed twice with hot ethylacetate to remove the reactant and product. The hot ethyl acetatewas removed from the reaction mixture and the resulting crudeproduct was purified by a column chromatography using silicagel 260 mesh (pet ether:ethyl acetate) ratio (25:75). The recov-ered catalyst was reused for the next run. All the products werecharacterized by1H and13C NMR spectra.Step 1 4-(2-((3R, 4aR, 6aS, 7R, 10bR)-3-cyclopentyl-6a, 10b-dimethyl-8-dihydromethylene decahydro-1H-naphtho[2, 1-d][1, 3]dioxin-7-yl)ethoxy)-3-fluoropyridine 3-Fluoropyridin-4-ol (33 mg, 0.29 mmol) was dissolved in anhydrous N, N-dimethylformamide (10 mL), and potassium carbonate (67.2 mg, 0.49 mmol) and (3R, 4aR, 6aS, 7R, 10bR)-7-(2-bromoethyl)-3-cyclopentyl-6a, 10b-dimethyl-8-methylenedecahydro-1H-naphtho[2, 1-d][1, 3]dioxin (100 mg, 0.24 mmol) were successively added to the reaction mixture and stirred at 60 C. overnight. The reaction solution was cooled and extracted with dichloromethane (30 mL). The organic layer was washed with water (10 mL*3), dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure and separated on a thin layer chromatography plate to give 4-(2-((3R, 4aR, 6aS, 7R, 10bR)-3-cyclopentyl-6a, 10b-dimethyl-8-dihydromethylene decahydro-1H-naphtho[2, 1-d][1, 3]dioxin-7-yl)ethoxy)-3-fluoropyridine 344 (55 mg, yield: 51.0%). MS m/z (ESI): 460.3 [M+1] 1H NMR (400 MHz, CDCl3) 8.37 (s, 3H), 8.29 (s, 3H), 6.86 (s, 3H), 4.90 (s, 1H), 4.61-3.95 (m, 5H), 3.51-3.43 (m, 2H), 2.45-1.53 (m, 18H), 1.51 (s, 3H), 1.37-1.25 (m, 3H), 0.879 (s, 3H).General procedure: In a typical reaction, 10 molpercent CuSO4·5H2O, (0.049 g, 0.2 mmol)and 6.7 molpercent EA (20 mg) were mixed in methanol followed by2 mmol of phenylboronic acid. This reaction mixture was kept ina preheated oil bath by maintaining the temperature at 60 °C andstirred under atmospheric pressure. After completion of the reac-tion, modified by TLC, the mixture was washed twice with hot ethylacetate to remove the reactant and product. The hot ethyl acetatewas removed from the reaction mixture and the resulting crudeproduct was purified by a column chromatography using silicagel 260 mesh (pet ether:ethyl acetate) ratio (25:75). The recov-ered catalyst was reused for the next run. All the products werecharacterized by1H and13C NMR spectra.General procedure: In a typical reaction, 10 mol% CuSO4·5H2O, (0.049 g, 0.2 mmol)and 6.7 mol% EA (20 mg) were mixed in methanol followed by2 mmol of phenylboronic acid. This reaction mixture was kept ina preheated oil bath by maintaining the temperature at 60 C andstirred under atmospheric pressure. After completion of the reac-tion, modified by TLC, the mixture was washed twice with hot ethylacetate to remove the reactant and product. The hot ethyl acetatewas removed from the reaction mixture and the resulting crudeproduct was purified by a column chromatography using silicagel 260 mesh (pet ether:ethyl acetate) ratio (25:75). The recov-ered catalyst was reused for the next run. All the products werecharacterized by1H and13C NMR spectra.EXAMPLE 83 7 (3-fluoropyridin-4-yl)oxy}-5-{ [2-methoxy-4-(pipeTazm- l -yl)phenyl]arnino}pyridof , 4- d]pyridazin-4-ol EXAMPLE 83A tert-butyl 4-(4-((7-((3-fluoropyridin-4-yl)oxy)-4-oxo-3, 4-dihydropyrido[3, 4-d]pyridazin-5- yl)amino)-3-methoxyphenyl)piperazine- 1 -carboxy late A mixture of EXAMPLE 24A (200 mg, 0.41 mmol), To a Biotage Atlantis reactor was added STR27 6-Nitro-7-(3-fluoro-4-oxo-4H-pyridin-1-yl)-1, 4-dihydroquinoxaline-2, 3-dione First, 127 mg of 7-fluoro-6-nitro-1, 4-dihydroquinoxaline-2, 3-dione, 96 mg of

Molecular Weight:113.09
XLogP3:0.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Exact Mass:113.027691913
Monoisotopic Mass:113.027691913
Topological Polar Surface Area:29.1
Heavy Atom Count:8
Complexity:171
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes