반응 #45433

반응 방정식

mixture

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

4-phenoxyphenylboronic acid

sodium carbonate

→

desired product

수율 55.0%

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

수율 55.0%

용매

1,2-dimethoxyethane

water

반응 조건

후처리

1. 1
   온도to reflux for 15 hours
2. 2
   농축concentrated under reduced pressure
3. 3
   추출The mixture was extracted with dichloromethane
4. 4
   건조the extract was dried (MgSO4)
5. 5
   여과filtered
6. 6
   농축concentrated
7. 7
   기타The residue was purified by flash column chromatography on silica gel

실험 절차

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)+.

출처