1,2-Dimethoxyethane → (2S)-ethyl 2-tert-butoxy-2-(2,7-dimethyl-5-(3,5,6,7-tetrahydro-2H-[1,4]oxazino[2,3,4-ij]quinolin-8-yl)quinolin-6-yl)acetate

Participants

Reaction Conditions

Reaction Steps

Preparation of (2S)-ethyl 2-tert-butoxy-2-(2,7-dimethyl-5-(3,5,6,7-tetrahydro-2H-[1,4]oxazino[2,3,4-ij]quinolin-8-yl)quinolin-6-ypacetate: A Smith process vial was charged with (S)-ethyl 2-(5-bromo-2,7-dimethylquinolin-6-yl)-2-tert-butoxyacetate (52 mg, 0.133 mmol, 1 eq.), 8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,5,6,7-tetrahydro-2H-[1,4]oxazino[2,3,4-ij]quinoline (48 mg, 0.159 mmol.), Pd(PPh3)4 (15 mg, 10%) and flushed with nitrogen. Dimethoxyethane (1.6 mL) and 2 M K2CO3 (0.24 mL, 0.48 mmol) was added. The reaction was heated in oil bath at 80° C. for 5 hours. The reaction mixture was diluted with ethyl acetate and washed with brine, dried (MgSO4), filtered, concentrated and purified by flash column chromatography (silica gel, 0 to 20% ethyl acetate/hexanes) to give (2S)-ethyl 2-tert-butoxy-2-(2,7-dimethyl-5-(3,5,6,7-tetrahydro-2H-[1,4]oxazino[2,3,4-ij]quinolin-8-yl)quinolin-6-yl)acetate as atropisomer mixture (39 mg, 60%). LCMS-ESI+: calcd for C30H37N2O4: 489.52 (M+H+). Found: 489.3.

Provenance & Evidence