N-(2-methoxyethyl)aniline

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: From 8-(4-benzyloxy-phenyl)-3-methyl-7-oxo-3,7-dihydro-imidazo [4,5-a]quinolizine-10-carboxylic acid with SOCl2 and DMF in toluene and treatment with triethylamine and (2-methoxy-ethyl)-phenyl-amine in dichloromethane.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: From 8-[p-(benzyloxy)phenyl]-7-oxo-7H-thieno[2,3-a]quinolizine-10-carboxylic acid with SOCl2 and DMF in toluene. Then treatment with triethylamine and (2-methoxy-ethyl)-phenyl-amine in dichloromethane.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: From 8-(4-benzyloxy-phenyl)-3-methyl-7-oxo-3,7-dihydro-imidazo[4,5-a]quinolizine-10-carboxylic acid with SOCl2 and DMF in toluene and treatment with triethylamine and (2-methoxy-ethyl)-phenyl-amine in dichloromethane.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound was prepared from aniline and methoxyacetaldehyde by the same method as described for Example 5, part A. The residue was purified by flash chromatography on silica gel (ethyl acetate:hexanes/1:15) to give a pale yellow oil. The residue was purified by flash chromatography on silica gel (ethyl acetate:hexanes/1:15) to give a pale yellow oil

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To phenylboronic acid (5 g, 41.0 mmol) in DCM (50 mL) was added copper (II) acetate (0.78 g, 4.1 mmol) and the mixture was stirred for 5 min at room temperature. 2-Methoxyethanamine (3.08 g, 41.0 mmol) was added and the mixture was stirred at 40 C for 19 h. The mixture was then passed through a silica plug and then purified by FCC, eluting with 10% EtOAc in heptane to afford the title compound (1.065 g, 17% yield). Method B HPLC-MS: MH+ requires m/z=152 Found: m/z=152, Rt=1.08 min (87%). the mixture was stirred at 40 C for 19 h purified by FCC eluting with 10% EtOAc in heptane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The general procedure under argon or air was followed using copper(I) iodide (10 mg, 0.05 mmol or 2.0 mg, 0.01 mmol), K3PO4 (425 mg, 2.00 mmol), 2-methoxyethylamine (104 μL, 1.20 mmol), iodobenzene (112 μL, 1.00 mmol), ethylene glycol (111 μL, 2.00 mmol) and 2-propanol (1.0 mL). Column chromatography using a solvent mixture (hexane/ethyl acetate=10/1, Rf=0.2) afforded N-(2-methoxyethyl)aniline (138 mg, 91% isolated yield) as colorless liquid. The spectral data (1H NMR) matched with the literature references and GC analysis indicated >95% purity. See Fancher, L. W.; Gless, R. D., Jr.; Wong, R. Y. Tetrahedron Lett. 1988, 29, 5095-5098.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: From 8-(4-benzyloxy-phenyl)-3-methyl-7-oxo-3,7-dihydro-imidazo [4,5-a]quinolizine-10-carboxylic acid with SOCl2 and DMF in toluene and treatment with triethylamine and (2-methoxy-ethyl)-phenyl-amine in dichloromethane.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: From 8-[p-(benzyloxy)phenyl]-7-oxo-7H-thieno[2,3-a]quinolizine-10-carboxylic acid with SOCl2 and DMF in toluene. Then treatment with triethylamine and (2-methoxy-ethyl)-phenyl-amine in dichloromethane.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: From 8-(4-benzyloxy-phenyl)-3-methyl-7-oxo-3,7-dihydro-imidazo[4,5-a]quinolizine-10-carboxylic acid with SOCl2 and DMF in toluene and treatment with triethylamine and (2-methoxy-ethyl)-phenyl-amine in dichloromethane.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: From 8-(4-benzyloxy-phenyl)-3-methyl-7-oxo-3,7-dihydro-imidazo[4,5-a]quinolizine-10-carboxylic acid with SOCl2 and DMF in toluene and treatment with triethylamine and (2-methoxy-ethyl)-phenyl-amine in dichloromethane.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound was prepared from aniline and methoxyacetaldehyde by the same method as described for Example 5, part A. The residue was purified by flash chromatography on silica gel (ethyl acetate:hexanes/1:15) to give a pale yellow oil. The residue was purified by flash chromatography on silica gel (ethyl acetate:hexanes/1:15) to give a pale yellow oil

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound was prepared from aniline and methoxyacetaldehyde by the same method as described for Example 5, part A. The residue was purified by flash chromatography on silica gel (ethyl acetate:hexanes/1:15) to give a pale yellow oil. The residue was purified by flash chromatography on silica gel (ethyl acetate:hexanes/1:15) to give a pale yellow oil