Morpholine → HCID 59519519, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-bromo-2-chloropyridin-3-amine (Small Molecules, Inc.) (1.000 g, 4.82 mmol) in pyridine (8 mL) was added 4-dimethylaminopyridine (Aldrich) (0.147 g, 1.205 mmol) and morpholine (Aldrich) (0.546 mL, 6.27 mmol). The reaction mixture was cooled to −30° C. and allowed the mixture to stir for 10 minutes. Then sulfuryl chloride (Aldrich) (0.586 mL, 7.23 mmol) was added dropwise into the reaction mixture. After the addition, the mixture was allowed to stir an additional 20 min. in the cooling bath then was allowed to warm to rt and continued to stir under N2 for 20 h. The reaction mixture was poured into the beaker which filled with EtOAc (50 mL) and hand stirred for 10 minutes. The organic layer was decanted into a round-bottom flask. The original mixture (black paste) was dissolved into DCM (3 ml) followed by adding EtOAc (20 mL) and hand stirred for 10 min and decanted to the same round-bottom flask that was mentioned earlier. The combined organic layers were concentrated in-vacuo. The crude product was purified by column chromatography (80 g, 10% to 20% acetone in hexanes) to obtain the desired product as light yellow solid (800 mg). MS (ESI pos. ion) m/z: 356.8. 1H NMR (300 MHz, CDCl3) δ ppm 3.15-3.41 (m, 4H) 3.60-3.83 (m, 4H) 6.79 (br. s., 1H) 8.08 (s, 1H) 8.23 (s, 1H).

Provenance & Evidence