6-Methoxy-3-pyridinylamine → HCID 59263506, compound

Participants

Reaction Steps

To an oven-dried 2-neck 25 mL round bottom flask equipped with a condenser was charged with 4′-bromo-1′-pentylspiro-(6,7-dihydrofuro-[2,3-f][1,3]benzodioxole-7,3′-indole)-2′-(1′H)-one (50.5 mg, 0.12 mmol), 5-amino-2-methoxypyridine (22.3 mg, 0.18 mmol), Pd2(dba)3 (10 mole %), BINAP (10 mole %) and sodium methoxide (12.9 mg, 0.24 mmol). The flask was flushed with nitrogen for 5 min followed by the addition of degassed toluene (5.00 mL). The reaction mixture was heated at reflux for 16 h. After cooling to ambient temperature, the reaction mixture was diluted with ethyl acetate (20.0 mL) and washed with saturated ammonium chloride (10.0 mL), brine (10.0 mL), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to dryness. The brown residue was subjected to column chromatography eluting with ethyl acetate-hexane (20% to 50%) to yield the title compound (30.0 mg) in 54% yield: MS (ES+), m/z 474.3 (M+1).

Provenance & Evidence