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tert-Butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-1(2H)-pyridinecarboxylate[ No CAS ]
[ 151273-41-5 ]
Yield
Reaction Conditions
Operation in experiment
54%
With sodium carbonate In 1,4-dioxane; water at 120℃; for 2h; Microwave irradiation;
95
terf-Butyl 4-(5-nitro-lJH-indol-3-yl)-5,6-dihydropyridine-l(2JH)-carboxylate; The mixture of tert-buty S-bromo-S-nitro-1H-indole-1-carboxylate (341.2 mg, 1.0 mmol, 1.0 eq), tert-butyl 4-(4,4,5,5-tetramethyl-l ,3,2-dioxaborolan-2-yl)-5,6- dihydropyridine-l(2H)-carboxylate (309.2 mg, 1.0 eq), (PPh3)4Pd (0) (231.1 mg, 0.2 eq), Na2CO3 (2M, 1.5 mL, 3.0 eq) and dioxane (1OmL) was degassed and heated at 120 °C in a microwave-oven synthesizer for 2 h. The mixture was cooled to room temperature and filtered fthrough a celite pad to remove Na2CO3 and catalyst. EtOAc was used to wash the celite pad. The solvent was removed and the crude was purified by silica gel with chromatography (0%~20% MeOH/DCM) to obtain the desired product tert-butyl 4-(5-nitro-1H-indol-3-yl)-5,6-dihydropyridine-l(2H)-carboxylate (184.1 mg, isolated yield 54%).