Reacción #2329004

ord-9e490c376a294c6b9abad52ed81ec33c

Ecuación de reacción

COc1ccc(C=Nc2ccc(O)cc2O)cn1
4-{[(6-methoxypyridin-3-yl)methylene]amino}benzene-1,3-diol
N#CC1=C(C#N)C(=O)C(Cl)=C(Cl)C1=O
DDQ
COc1ccc(-c2nc3ccc(O)cc3o2)cn1
title compound
COc1ccc(-c2nc3ccc(O)cc3o2)cn1
2-(6-Methoxypyridin-3-yl)-1,3-benzoxazol-6-ol

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    workup.ADDITIONSiO2 was added
  2. 2
    Otrothe solvents were removed under reduced pressure
  3. 3
    OtroThe crude product was purified by flash column chromatography

Procedimiento

4-{[(6-methoxypyridin-3-yl)methylene]amino}benzene-1,3-diol was dissolved in CH2Cl2 (30 mL) and DDQ was added. The reaction mixture was stirred over night at r.t., SiO2 was added and the solvents were removed under reduced pressure. The crude product was purified by flash column chromatography to give the title compound (189.1 mg). 1H NMR δ ppm 9.88 (s, 1H) 8.90 (dd, 1H) 8.35 (dd, 1H) 7.56 (d, 1H) 7.09 (d, 1H) 6.85 (dd, 1H) 3.95 (s, 3H); MS m/z 243 (M+H).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07670591B2uspto-grants-2010_03