Reacción #165618

Ecuación de reacción

product

3-(2-Methoxy-ethyl)-4,5-dimethyl-3H-thiazol-2-ylideneamine

Et3N

5-bromo-2,3-dihydrobenzo[b]-furan-7-carbonyl chloride

→

title compound

Rendimiento 36.0%

5-bromo-N-[(2Z)-3-(2-methoxyethyl)-4,5-dimethyl-1,3-thiazol-2(3H)-ylidene]-2,3-dihydro-1-benzofuran-7-carboxamide

Rendimiento 36.0%

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe resulting crude material was purified via flash column chromatography (SiO2, 7:3 hexanes:EtOAc)

Procedimiento

The product of Example 126A (0.20 g, 1.1 mmol), Et3N (0.45 mL, 3.2 mmol) and 5-bromo-2,3-dihydrobenzo[b]-furan-7-carbonyl chloride (Maybridge, 0.42 g, 1.6 mmol) in 35 mL THF were processed as in Example 126B. The resulting crude material was purified via flash column chromatography (SiO2, 7:3 hexanes:EtOAc) to afford the title compound (0.16 g, 0.39 mmol, 36% yield). 1H NMR (300 MHz, CDCl3) δ ppm 2.24 (s, 3H), 2.28 (s, 3H), 3.23 (t, J=8.5 Hz, 2H), 3.33 (s, 3H), 3.78-3.87 (m, 2H), 4.45-4.56 (m, 2H), 4.70-4.81 (m, 2H), 7.35-7.39 (m, 1H), 8.09 (d, J=2.0 Hz, 1H); MS (DCI/NH3) m/z 411, 413 (M+H)+; Anal. calculated for C17H19BrN2O3S.0.3H2O: C, 49.00; H, 4.74; N, 6.72. Found: C, 48.91; H, 4.36; N, 6.57.

Fuente