Sodium Carbonate → HCID 59118256, compound

Participants

Reaction Conditions

Reaction Steps

3,4-Dichlorophenylboronic acid (34 mg, 0.18 mmol), a solution of palladium acetate (3 mg, 0.01 mmol) and triphenylphosphine (12 mg, 0.05 mmol) in toluene (1 mL), and 2 M aqueous sodium carbonate (1 mL) were added successively to a solution of tert-butyl (2R)-2-hydroxy-2-(3-pyridinyl)ethyl{[(2R)-6-iodo-3,4-dihydro-2H-chromen-2-yl]methyl}carbamate (Example 37, 60 mg, 0.12 mmol) in toluene (2 mL). The mixture was heated (80° C.) and stirred for 16 hours. After cooling the reaction was diluted with dichloromethane (5 mL) and the layers were separated. The organic layer was concentrated in vacuo and the residue was dissolved in a solution of 4 M hydrogen chloride in dioxane (4 mL). The solution was stirred for 16 hours and then concentrated in vacuo. Preparative reverse phase HPLC of the residue using acetonitrile/water afforded 10.3 mg (20%) of the desired product (retention time=2.19 min.): 1H NMR (CD3OD, δ): 8.71 (d, J=2.2 Hz, 1 H), 8.59 (dd, J=5.1, 1.5 Hz, 1 H), 8.11 (ddd, J=7.9, 1.7, 1.7 Hz, 1 H), 7.71 (d, J=2.3 Hz, 1 H), 7.61 (dd, J=7.9, 5.1 Hz, 1 H), 7.37-7.56 (m, 4 H), 6.99 (d, 9.2 Hz, 1 H), 5.22 (dd, J=10.5, 2.9 Hz, 1 H), 4.43-4.54 (m, 1 H), 3.26-3.55 (m, 4 H), 2.87-3.10 (m, 2 H), 2.11-2.22 (m, 1 H), 1.76-1.92 (m, 1 H); mass spectroscopy gave m/z=429.2 [M+H]+.

Provenance & Evidence