HCID 20484885, compound → ethyl 2-[4-[N-(7-fluoroisoquinolin-3-yl)-N-methylamino]phenoxy}propionate
Reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([F:12])[CH:10]=2)[CH:5]=[C:4]([N:13]([C:15]2[CH:28]=[CH:27][C:18]([O:19][CH:20]([CH3:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:17][CH:16]=2)[CH3:14])[N:3]=1>C(O)(=O)C.[Zn]>[F:12][C:9]1[CH:10]=[C:11]2[C:6]([CH:5]=[C:4]([N:13]([C:15]3[CH:28]=[CH:27][C:18]([O:19][CH:20]([CH3:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:17][CH:16]=3)[CH3:14])[N:3]=[CH:2]2)=[CH:7][CH:8]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
Zinc powder (4×1.63 g) was added portionwise over a 2 hr period to a stirred solution of ethyl 2-{4-[N-(1-chloro-7-fluoroisoquinolin-3-yl)-N-methylamino]phenoxy}propionate (1.00 g) in acetic acid (50 ml). The mixture was filtered and the filter cake was washed with acetic acid. After the filtrate was evaporated the residue was partitioned between methylene chloride and water. The organic extract was washed successively with, aqueous sodium bicarbonate solution, water, aqueous ethylenediaminetetraacetic acid solution (5%) and water, then dried (MgSO4) and evaporated to give a green oil. Purification by column chromatography over silica gel (eluant dichloromethane) gave ethyl 2-[4-[N-(7-fluoroisoquinolin-3-yl)-N-methylamino]phenoxy}propionate (0.55 g) as a greenish oil. The assigned structure was confirmed by proton magnetic spectroscopy and mass spectrometry. Proton magnetic resonance spectrum (CDCl3 ; δ in ppm): 1.28 (3H, t); 1.64 (3H, d); 3.48 (3H, s); 4.25 (2H, q); 4.74 (1H, q); 6.62 (1H; s); 6.87-7.37 (7H, m); 8.85 (1H, s).