Potassium Carbonate → HCID 54767213, compound

Participants

Reaction Conditions

Reaction Steps

2-hydroxypyridine-1-oxide (0.04 g, 0.34 mmol) was dissolved in 5 mL of anhydrous DMF. To this was added K2CO3 (0.14 g, 1.02 mmol) and 4-bromomethylphenyl boronic acid pinacol ester (0.10 g, 0.34 mmol). The reaction was heated to 80° C. and allowed to stir under nitrogen overnight. After cooling to room temperature, the solvent was evaporated and the resulting residue was brought up in dichloromethane and washed twice with water. The organic layer was dried over MgSO4, filtered and concentrated for purification via silica gel chromatography eluting with 2% MeOH in DCM. The protected B19 was collected as an off-white solid in 87% yield (98 mg, 0.3 mmol). 1H NMR (400 MHz, CDCl3) δ=7.79 (d, J=8.0 Hz, 2H), 7.38 (d, J=8.0 Hz, 2H), 7.24 (td, J=7.2 Hz, J2=2.0 Hz, 1H), 7.05 (dd, J=7.2 Hz, J2=2.0 Hz, 1H), 6.67 (dd, J=9.2 Hz, J2=1.2 Hz, 1H), 5.89 (td, J=6.8 Hz, J2=1.6 Hz, 1H), 5.29 (s, 2H), 1.35 (s, 12H). 13C NMR (100 MHz, CDCl3) δ=159.2, 138.9, 137.0, 136.8, 135.3, 129.5, 122.9, 104.7, 84.3, 78.4, 25.1. ESI-MS(+): m/z 328.18 [M+H]+. Anal. calcd. for C18H22BNO4. 0.4 CH3OH: C, 65.26; H, 6.94; N, 4.16. Found: C, 65.54; H, 7.20; N, 3.76.

Provenance & Evidence