Dimethylformamide → HCID 59272318, compound

Participants

Reaction Conditions

Reaction Steps

(4S)-2′-Bromo-7′-(2-pyridinyloxy)spiro[1,3-oxazole-4,9′-xanthen]-2-amine (380 mg, 0.896 mmol), copper(i) iodide (34.1 mg, 0.179 mmol), tetrakis(triphenylphosphine)palladium (104 mg, 0.090 mmol), 3,3-dimethylbut-1-yne (221 mg, 2.69 mmol) and DMF (3583 μL, 0.896 mmol) were combined in a sealable tube. The reaction vessel was flushed with argon then di-isopropyl amine (3766 μL, 26.9 mmol) was added and the vessel was sealed and heated at 90° C. for 2 hours. The reaction was diluted with water (50 mL) and poured into a separatory funnel containing ethyl acetate (50 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (3×50 mL). The combined organic layers were washed with water and then brine, dried over sodium sulfate, filtered and concentrated in vacuo to provide a brown foam that was purified by silica gel chromatography (Redi-Sep pre-packed silica gel column (40 g), 0-10% methanol in methylenechloride with 0.1% ammonium hydroxide) to (4R)-2′-(3,3-dimethyl-1-butyn-1-yl)-7′-(2-pyridinyloxy)spiro[1,3-oxazole-4,9′-xanthen]-2-amine (245 mg, 0.576 mmol, 64.3% yield) as a light yellow solid. MS m/z=426.2 [M+H]+. Calc'd for C26H24N3O3: 426.2.

Provenance & Evidence