CHEMBRDG-BB 5144041

To a solution of 0.75 g (2.45 mmol) of .4 in 10 ml. dimethyl formamide was added 0.68 g (4.90 mmol) Cs2C03 followed by 0.53 g (2.70 mmol) To a solution of 2.8 g (9.47 mmol) of compound 1 step 4 in 38 ml. tetrahydrofurane was added 3.09 g (9.47 mmol) of cesium carbonate, followed by 1.86 g (9.47 mmol) of ethyl 2-(2- hydroxyphenoxy)acetate (CAS 99186-63-7). The mixture was refluxed for 96 hours. The mixture was filtered and the solvent was removed under reduced pressure. The crude mixture was then dissolved in 50 ml. EtOH , acidified to pH 3-4 by addition of cone. H2SO4 and stirred at room temperature for 18 hours. The solvent was removed under reduced pressure, water was added and the mixture was extracted with ethyl acetate. The combined organic layer was washed with sat. aqueous NaCI, dried over anhydrous MgS04, filtered and the solvent was removed under reduced pressure. The crude product was purified by column chromatography on silica (petrol ether/ethyl acetate) to give 3.20 g (6.77 mmol, 71 %) of the desired compound 1. 1 H-NMR (CDCI3, ppm): 7.75 (d, J=7.77 Hz, 1 H); 7.23 (dd, J=7.91 Hz, J=1.63 Hz, 1 H); 7.19 (ddd, J=8.17 Hz, J=7.57 Hz, J=1.67 Hz, 1 H);7.04 (dt, J=7.77 Hz, J=7.77 Hz, J=1.46 Hz, 1 H); 6.95 (t, J=58.13 Hz, 1 H); 6.93 (dd, J=8.18 Hz, J=1.44 Hz, 1 H); 4.57 (s, 2 H); 4.15 (q, J=7.14 Hz, 2 H); 2.37 (s, 3 H); 1.21 (t, J=7.14 Hz, 3 H). [M+H] = 473.1 ; Rt = 1.226 min.To a solution of 40 g (0.24 mol) 3-chloro-2, 5, 6-trifluoropyridine (CAS 2879-42-7) in 400 ml. di- methyl sulfoxide at 23C was added 17 g (0.26 mol) of sodium azide. The mixture was stirred 16 hours at 23C. Then a suspension of 49 g (0.25 mol)

Molecular Weight:196.20
XLogP3:1.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:5
Exact Mass:196.07355886
Monoisotopic Mass:196.07355886
Topological Polar Surface Area:55.8
Heavy Atom Count:14
Complexity:181
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes