Cesium fluoride → HCID 86700880, compound

Participants

Reaction Conditions

Reaction Steps

To a flask charged with methyl 3-(4-(4-bromophenyl)-7-oxabicyclo[2.2.1]heptan-1-yl)propanoate (103 mg, 0.30 mmol), 5-(tert-butyl)-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,4-oxadiazol-2-amine (109 mg, 0.32 mmol), Pd(amphos)Cl2 (21 mg, 0.030 mmol) and CsF (138 mg, 0.91 mmol) under N2 was added 1,4-dioxane (2.7 mL) and water (0.30 mL). The mixture was sparged with N2 for 10 min and stirred in a 90° C. oil bath for 2 h. The resulting reaction mixture was diluted with dichloromethane and washed with a saturated aqueous NaHCO3 solution. The organic layer was warmed and filtered (no product evident in filtercake). The filtrate was concentrated to afford 200 mg of crude orange solid. The crude material was washed with triturated with acetonitrile and filtered to afford 106 mg of pale orange solid which was used without further purification. 1H NMR (400 MHz, DMSO-d6): δ ppm 1.36 (s, 9H), 1.56-1.83 (m, 6H), 2.04-2.20 (m, 4H), 3.62 (s, 3H), 7.42 (d, J=8.6 Hz, 2H), 7.55-7.69 (m, 6H), 10.51 (s, 1H) (additional 2H signal likely hidden under DMSO solvent peak). ESI-MS m/z: 476.0 [M+H]+, retention time 1.55 min (condition E).

Provenance & Evidence