Sodium Bicarbonate → HCID 135900033, compound

Participants

Reaction Steps

(5-Cyano-2-nitro-phenyl)-(5-morpholin-4-ylmethyl-pyridin-2-yl)-acetic acid ethyl ester HCl (8.0 g, 17.9 mmol was slurried in toluene (80 ml) at room temperature and sodium hydrogen carbonate (7.52 g, 89.5 μmol) dissolved in water (50 ml) was added and the reaction mixture stirred at room temperature for 25 min. The organic phase was separated and washed with water and then concentrated to dryness and then redissolved in ethanol (80 ml) and the solution added to a preheated solution of ammonium sulphide (26 ml, 21 w/w %, 107.4 mmol) in water at 50° C. over 20 mins. The resulting yellow slurry was stirred for 1 hr at 50° C. then cooled in an ice bath. The slurry was filtered and washed with water followed by isopropanol. After drying at 50° C. under vacuum gave a yellow powder, 6.67 g, (purity 94%), 76% yield of 1,2-Dihydroxy-3-(5-morpholin-4-ylmethyl-pyridin-2-yl)-1H-indole-5-carbonitrile. 1H NMR (400 MHz; d6-DMSO,): δ 14.36 (br s, 1H), 10.86 (br s, 1H), 8.12 (s, 1H), 7.96 (s, 1H), 7.88 (br d, 1H), 7.87 (br d, 1H), 7.78 (br dd, 1H), 7.36 (dd, J=1.0, 8.0 Hz, 1H), 7.08 (d, H=8.1 Hz, 1H), 3.56 (t, J=4.0, 8.2 Hz, 4H), 3.37 (s, 2H), 2.27 (br s, 4H); 13C NMR: (100 MHz, d6-DMSO): δ 163.8, 148.8, 142.7, 136.7, 136.1, 123.1, 121.5, 120.4, 119.4, 119.1, 102.0, 81.9, 67.2, 66.6, 58.8, 53.3 ppm; MS (ESI) m/z [M+1]+ 351.

Provenance & Evidence