4-Amino-2-fluoropyridine

Synthesis of (R)-N-(2-fluoropyridin-4-yl)-1, 2, 4-trimethyl-5-(2-oxo-2-((1, 1, 1-trifluoropropan-2-yl)amino)acetyl)-1H-pyrrole-3-carboxamide The title compound was prepared following the procedure described in Example 2, substituting General procedure: To a stirred solution of 2-fluoro-5-aminopyridine (168 mg, 1.50 mmol) in THF (10 mL) were dropwise added at 0 C ethyl chloroglyoxylate (110 muL, 1.00 mmol) and Et3N (210 muL, 1.50 mmol). The mixture was stirred at room temperature for 24 h. After the precipitate was filtrated off, the filtrate solution was concentrated under reduced pressure. The residue was dissolved in EtOAc, and washed with 1.0 M HCl, saturated NaHCO3 and brine, then dried over Na2SO4. Concentration under reduced pressure provided the amidoester (268 mg) as brown oil, which was used without further purification. To a solution of the amidoester (150 mg) in EtOH (5 mL) were added Et3N (246 muL, 1.78 mmol) and 2, 2, 6, 6-tetramethylpiperidin-4-amine (190 muL, 1.07 mmol). The reaction mixture was stirred for 2 h at 150 C under microwave irradiation. After being concentrated in vacuo, the residue was extracted with CHCl3, and washed with saturated NaHCO3 and brine, then dried over Na2SO4. Concentration under reduced pressure followed by flash chromatography over silica gel with CHCl3-MeOH (10: 1) provided the title compound 16 (73.3 mg, 41% yield) as white powder.To a solution of ethyl 2-((5-(trifl uoromethyl)benzo[d]oxazol-2-yl)amino)thiazole-4- carboxylate (400mg, 1.lmmol) and To a solution of CuCl2 dihydrate (0.0680 g, 0.41 mmol) was dissolved in 4 mL of water to yield a light bluesolution. A solution of 2-F-4AP (0.117 g, 1.04 mmol) in 7.5 mL of 1.5 M HCl (aq) was added tothe CuCl2 solution. The resulting light blue-green solution was left to evaporate at roomtemperature for two months. Orange plates were recovered by vacuum filtration, washedwith cold water and allowed to air dry to give 0.0893 g (60%). CHN Calcd (found) forC10H12N4F2Cl4Cu; C, 27.83 (28.14); H, 2.80 (2.98); N, 12.98 (13.11) %. IR (KBr) nu - 3383 m, 3309 m, 3207 m, 3092 m, 2964 m, 2927 m, 1663 s, 1607 s, 1525 m, 1208 m, 1006 m, 850 w, 837 w, 776w, 543 m, 527 w, and 477 m cm-1.

Molecular Weight:112.10
XLogP3:0.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Exact Mass:112.04367633
Monoisotopic Mass:112.04367633
Topological Polar Surface Area:38.9
Heavy Atom Count:8
Complexity:76.8
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes