Toluene → Ethyl 1-((1-(2-methoxyethyl)-1,2,3,4-tetrahydroquinolin-7-yl)methyl)-1H-pyrazole-4-carboxylate

Participants

Reaction Conditions

Reaction Steps

(1-(2-Methoxyethyl)-1,2,3,4-tetrahydroquinolin-7-yl)methanol (357 mg, 0.807 mmol) and ethyl 1H-pyrazole-4-carboxylate (113 mg, 0.807 mmol) were dissolved in THF (5 ml). Triphenylphosphine (317 mg, 1.210 mmol) was added, and, after cooling to 0° C., a 40% solution of DEAD in Toluene (0.479 ml, 1.210 mmol) was added dropwise. The reaction mixture was stirred for 2 hr at 0° C., then overnight at 20° C. The reaction mixture was diluted with AcOEt and washed with 1N HCl, and saturated aqueous NaHCO3. The organic layer was dried over MgSO4 and concentrated under reduced pressure. The crude product was purified by preparative-HPLC (Waters SunFire Prep C18 OBD 5 μm 19*50, Flow 20 mL/min, ACN: 2 min at 5%, then to 100% within 17.5 min, RT 11.80 min) to give the title compound. HPLC (Method A) Rt=2.001 min; MS (Method A) [M]+=343.9

Provenance & Evidence