Reacción #45433

Ecuación de reacción

mixture

3-bromo-7-[(1E)-3,3-diethoxy-1-propenyl]thieno[3,2-c]pyridin-4-amine

4-phenoxyphenylboronic acid

sodium carbonate

→

desired product

Rendimiento 55.0%

7-[(1E)-3,3-diethoxy-1-propenyl]-3-(4-phenoxyphenyl)thieno[3,2-c]pyridin-4-amine

Rendimiento 55.0%

Disolventes

1,2-dimethoxyethane

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturato reflux for 15 hours
2. 2
   Concentraciónconcentrated under reduced pressure
3. 3
   ExtracciónThe mixture was extracted with dichloromethane
4. 4
   Secadothe extract was dried (MgSO4)
5. 5
   Filtraciónfiltered
6. 6
   Concentraciónconcentrated
7. 7
   OtroThe residue was purified by flash column chromatography on silica gel

Procedimiento

A mixture of Example 176A (250 mg, 0.70 mmol), 4-phenoxyphenylboronic acid (180 mg, 0.84 mmol), Pd(PPh3)4 (50 mg, 0.04 mmol), and sodium carbonate (150 mg, 1.4 mmol) in 1,2-dimethoxyethane (8 mL) and water (4 mL) was heated to reflux for 15 hours. The mixture was cooled to room temperature and concentrated under reduced pressure. The mixture was extracted with dichloromethane and the extract was dried (MgSO4), filtered, and concentrated. The residue was purified by flash column chromatography on silica gel to provide the desired product (170 mg, 55%). 1H NMR (DMSO-d6, 400 MHz) δ 8.00 (s, 1H), 7.56 (s, 1H), 7.47 (m, 4H), 7.20 (t, 1H), 7.13 (m, 4H), 6.81 (d, 1H), 6.17 (dd, 1H), 5.67 (br s, 2H), 5.13 (d, 1H), 3.57 (m, 4H), 1.18 (t, 6H); MS m/e 447.3 (M+H)+.

Fuente