Potassium Phosphate, Tribasic → HCID 86664220, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of potassium phosphate, tribasic (0.141 g, 0.665 mmol), potassium cyclopropyltrifluoroborate (0.049 g, 0.332 mmol), 8-chloro-2-methyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-6-carbaldehyde 15 (0.05 g, 0.222 mmol) in toluene (Ratio: 5.00, 5 mL) and water (Ratio: 1.000, 1.0 mL) was added PdOAc2 (3.73 mg, 0.017 mmol) and dicyclohexyl(2′,6′-diisopropoxybiphenyl-2-yl)phosphine (0.016 g, 0.033 mmol) at 23° C. The reaction was stirred at 110° C. for 14 hr. The reaction mixture was poured into water (2 mL) and extracted with Et2O (3×5 mL). The organic layer was dried over Na2SO4, filtered, and the organic phase stripped to dryness via rotary evaporation. The resulting crude material was reconstituted in DCM (0.25 mL) and purified via medium pressure chromatography using a gradient eluant of 1-5% MeOH:DCM. The appropriate fractions were combined and solvent was removed via rotary evaporation. The late eluting fractions were dried in vacuo to provide the title compound as an off-white solid (0.0283 g, 0.122 mmol, 55.2% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 0.69-0.81 (m, 2H) 0.91-1.04 (m, 2H) 1.48 (d, J=6.57 Hz, 3H) 2.15 (tt, J=8.49, 5.15 Hz, 1H) 4.85 (q, J=6.82 Hz, 1H) 7.13 (d, J=1.77 Hz, 1H) 7.19 (d, J=1.77 Hz, 1H) 9.79 (s, 1H) 10.89 (s, 1H). ESI-MS: m/z 232.1 (M+H)+.

Provenance & Evidence