Potassium Carbonate → [6s,9r,11r]2',3',4',5,5',6,7,8,9,10-Decahydro-2-(3-(2-pyridyl)-isoxazol-5-yl)-5'-(2,2,2-trifluoroethyl)-spiro[6,9-methanobenzocyclooctene-11,3'-[1,2,5]thiadiazole]1',1'-dioxide

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-(5-iodoisoxazol-3-yl)pyridine (prepared in the manner of Ku et al Org. Lett. 3 (26), 4185–4187, 2001.) (90 mg, 0.3 mmol), the homochiral boronate from Step 1 (100 mg, 0.2 mmol) potassium carbonate (135 mg, 1 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloro palladium (II) dichloromethane complex (5 mg) in toluene (2 mL), ethanol (1 mL) and water (1 mL) was heated under microwave conditions at 100° C. for 5 minutes. More [1,1′-bis(diphenylphosphino)ferrocene]dichloro palladium (II) dichloromethane complex (5 mg) was added and the mixture was again heated under microwave conditions at 100° C. for 5 minutes. The reaction was diluted with sodium bicarbonate (half sat, 20 mL) and extracted with ethylacetate (2×30 mL). The extracts were washed with brine, dried (MgSO4) and evaporated in vacuo to give a brown gum, which was purified by column chromatography, eluting with ethylacetate:iso-hexane (1:4) to give the title compound as a white solid (70 mg, 69%). δ (1H, 400 MHz, CDCl3) 1.32–1.40 (2H, m), 1.74–1.78 (2H, m), 2.48–2.52 (2H, m), 2.74–2.83 (2H, m), 3.26–3.31 (2H, m), 3.46 (2H, s), 3.70 (2H, q, J=8.7 Hz), 4.83 (1H, brs), 7.17 (1H, s), 7.23 (1H, d, J=8.3 Hz), 7.36–7.40 (1H, m), 7.60–7.62 (2H, m), 7.81–7.85 (1H, m), 8.12–8.14 (1H, m), and 8.71–8.72 (1H, m). MS (ES+) 505 ([MH]+).

Provenance & Evidence