十氢叔丁酯-2,7-萘啶-2-羧酸酯

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of tert-butyl octahydro-2,7-naphthyridine-2(1H)-carboxylate (320 mg, 1.33 mmol, 1 eq), chloro bromopropane (530 mg, 3.33 mmol, 2.5 eq) and K2CO3 (736 mg, 5.33 mmol, 4 eq) in acetone (25 mL) was heated to reflux overnight, then cooled to room temperature and filtered. The filtrate was concentrated in vacuo and the residue was purified by a silica gel column chromatography (20:1 (v/v) CH2Cl2/MeOH) to afford the title compound as pale yellow oil (190 mg, 47%). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 317.2 (M+1). was heated to reflux overnight filtered The filtrate was concentrated in vacuo the residue was purified by a silica gel column chromatography (20:1 (v/v) CH2Cl2/MeOH)

反应条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A suspension of tert-butyl 3,4-dihydro-2,7-naphthyridine-2(1H)-carboxylate (1.00 g, 4.27 mmol, 1 eq) and Pd(OH)2 (400 mg, 0.1 eq) in 150 mL of acetic acid was heated at 80° C. overnight under Hz, then cooled to room temperature, filtered and concentrated in vacuo. To this, 100 mL of water was added. The mixture was adjusted to pH 7-8 with NH3—H2O, extracted with CH2Cl2 (50 mL×3). The organic layer was dried over anhydrous Na2SO4 and concentrated in vacuo, and the residue was purified by a silica gel column chromatography (10:1 (v/v) EtOAc/MeOH) to give the title compound as pale yellow oil (700 mg, 69%). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 241.1 (M+1). cooled to room temperature filtered concentrated in vacuo To this, 100 mL of water was added extracted with CH2Cl2 (50 mL×3) The organic layer was dried over anhydrous Na2SO4 concentrated in vacuo the residue was purified by a silica gel column chromatography (10:1 (v/v) EtOAc/MeOH)

反应条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A suspension of tert-butyl 3,4-dihydro-2,7-naphthyridine-2(1H)-carboxylate (1.00 g, 4.27 mmol, 1 eq) and Pd(OH)2 (400 mg, 0.1 eq) in 150 mL of acetic acid was heated at 80° C. overnight under Hz, then cooled to room temperature, filtered and concentrated in vacuo. To this, 100 mL of water was added. The mixture was adjusted to pH 7-8 with NH3—H2O, extracted with CH2Cl2 (50 mL×3). The organic layer was dried over anhydrous Na2SO4 and concentrated in vacuo, and the residue was purified by a silica gel column chromatography (10:1 (v/v) EtOAc/MeOH) to give the title compound as pale yellow oil (700 mg, 69%). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 241.1 (M+1). cooled to room temperature filtered concentrated in vacuo To this, 100 mL of water was added extracted with CH2Cl2 (50 mL×3) The organic layer was dried over anhydrous Na2SO4 concentrated in vacuo the residue was purified by a silica gel column chromatography (10:1 (v/v) EtOAc/MeOH)

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of tert-butyl octahydro-2,7-naphthyridine-2(1H)-carboxylate (320 mg, 1.33 mmol, 1 eq), chloro bromopropane (530 mg, 3.33 mmol, 2.5 eq) and K2CO3 (736 mg, 5.33 mmol, 4 eq) in acetone (25 mL) was heated to reflux overnight, then cooled to room temperature and filtered. The filtrate was concentrated in vacuo and the residue was purified by a silica gel column chromatography (20:1 (v/v) CH2Cl2/MeOH) to afford the title compound as pale yellow oil (190 mg, 47%). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 317.2 (M+1). was heated to reflux overnight filtered The filtrate was concentrated in vacuo the residue was purified by a silica gel column chromatography (20:1 (v/v) CH2Cl2/MeOH)

反应条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A suspension of tert-butyl 3,4-dihydro-2,7-naphthyridine-2(1H)-carboxylate (1.00 g, 4.27 mmol, 1 eq) and Pd(OH)2 (400 mg, 0.1 eq) in 150 mL of acetic acid was heated at 80° C. overnight under Hz, then cooled to room temperature, filtered and concentrated in vacuo. To this, 100 mL of water was added. The mixture was adjusted to pH 7-8 with NH3—H2O, extracted with CH2Cl2 (50 mL×3). The organic layer was dried over anhydrous Na2SO4 and concentrated in vacuo, and the residue was purified by a silica gel column chromatography (10:1 (v/v) EtOAc/MeOH) to give the title compound as pale yellow oil (700 mg, 69%). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 241.1 (M+1). cooled to room temperature filtered concentrated in vacuo To this, 100 mL of water was added extracted with CH2Cl2 (50 mL×3) The organic layer was dried over anhydrous Na2SO4 concentrated in vacuo the residue was purified by a silica gel column chromatography (10:1 (v/v) EtOAc/MeOH)