Sodium Carbonate → 5-(4-(1-hydroxyethyl)pyridin-3-yl)-3-methylbenzo[d]oxazol-2(3H)-one

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-(3-Bromo-pyridin-4-yl)-ethanol (240 mg, 1.188 mmol), 3-Methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3H-benzooxazol-2-one (327 mg, 1.188 mmol), PalladiumTetrakis (270 mg, 0.030 mmol), sodium carbonate (2 M in water, 0.594 ml, 1.188 mmol) in 1,4-Dioxane (2 ml) was heated by microwave at 100° C. for 1 hr. After filtration, drying over Na2SO4, filtration again and concentration, the residue was purified by flash column (CH2Cl2-MeOH, v/v, 1%-4.5%) yielded an oil which was subsequently purified by chiral HPLC (Ethanol-Heptane, v/v, 20%, ChiralPak OD-H column) to peak 1 (enantiomer 1 retention time 9.21 min) and second peak (enantiomer 2, retention time 11.31 min). ESI-MS m/z: 271.2 [M+1]+, Retention time 0.93 min; 1H NMR (400.3 MHz, MeOD): δ 1.32 (d, J=6.4 Hz, 3H), 3.47 (s, 3H), 497 (q, J=6.4 Hz, 1H), 7.15 (dd, J=8.0, 2.0 Hz, 1H), 7.22 (d, J=2.0 Hz, 1H), 7.40 (d, J=8.0 Hz, 1H), 7.75 (d, J=5.6 Hz, 1H), 8.38 (s, 1H), 8.59 (d, J=5.6 Hz, 1H).

Provenance & Evidence