Phenyl isocyanate → HCID 68613235, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 4-nitrobutyrate (90 μL, 0.69 mmol, 3.0 equiv.) and 3-[[(1-methyl-2(S)-pyrrolidinyl)methoxy]-5-ethynylpyridine (50 mg, 0.23 mmol) in dry benzene (2.3 mL) were added phenyl isocyanate (80 μL, 0.69 mmol, 3.0 equiv.) and triethylamine (60 μL, 0.46 mmol, 2.0 equiv.). The reaction mixture was stirred at 60° C. for 24 h, then diluted with water and stirred vigorously for 2 h. The mixture was extracted with CH2Cl2, and the organic phase was dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by CC on SiO2 with CH2Cl2/MeOH 9:1 to give the isoxazole (80 mg, 98%). 1H NMR (CD3OD, 400 MHz) δ 8.58 (s, 1H), 8.39 (s, 1H), 7.57 (s, 1H), 6.51 (s, 1H), 4.09 (dd, 1H, J=9.2, 5.5 Hz), 4.02 (dd, 1H, J=9.2, 5.5 Hz), 3.73 (s, 3H), 3.15 (t, 1H, J=7.2 Hz), 3.07 (t, 2H, J=7.2 Hz), 2.80 (t, 2H, J=7.2 Hz), 2.73 (m, 1H), 2.51 (s, 3H), 2.36 (m, 1H), 2.07 (m, 1H), 1.85 (m, 3H).

Provenance & Evidence