반응 #45417

반응 방정식

NaCl

mixture

3-bromothieno[3,2-c]pyridin-4-amine

4-phenoxyphenylboronic acid

Na2CO3

→

desired product

수율 75.0%

3-(4-phenoxyphenyl)thieno[3,2-c]pyridin-4-amine

수율 75.0%

용매

water

DMF

반응 조건

후처리

1. 1
   추출extracted with ethyl acetate (3×70 mL)
2. 2
   세척The combined organic extracts were washed with brine
3. 3
   건조dried (MgSO4)
4. 4
   여과filtered
5. 5
   농축concentrated under reduced pressure
6. 6
   workup.DISSOLUTIONThe residue was dissolved in 300 mL of dichloromethane
7. 7
   workup.ADDITIONSilica gel (90 g) was added to the solution
8. 8
   농축the mixture was concentrated under vacuum
9. 9
   기타The residual silica gel with the absorbed crude product
10. 10
    기타chromatographed (eluent 40% ethyl acetate/heptane)

실험 절차

A mixture of Example 219A (5.43 g, 23.7 mmol), 4-phenoxyphenylboronic acid (6 g, 28.03 mmol), Na2CO3 (3.7 g, 34.9 mmol), Pd(PPh3)4 (5.4 g, 4.7 mmol), DMF (96 mL), and water (24 mL) was stirred for 18 hours at 80° C. under nitrogen, poured into 10% aqueous NaCl (400 mL), and extracted with ethyl acetate (3×70 mL). The combined organic extracts were washed with brine, dried (MgSO4), filtered, and concentrated under reduced pressure. The residue was dissolved in 300 mL of dichloromethane. Silica gel (90 g) was added to the solution and the mixture was concentrated under vacuum. The residual silica gel with the absorbed crude product was transferred to a silica gel column (600 g) and chromatographed (eluent 40% ethyl acetate/heptane) to provide 5.61 g (75%) of the desired product. 1H NMR (DMSO-d6, 400MHz) δ 7.85 (d, 1H), 7.49-7.44 (m, 5H), 7.29 (d, 1H), 7.22 (t, 1H), 7.16-7.12 (m, 4H), 5.44 (br s, 2H); 13C NMR (DMSO-d6, 100 MHz) δ 156.9, 156.1, 154.5, 148.3, 141.8, 136.1, 130.9, 130.1, 123.9, 123.0, 119.2, 118.4, 118.1, 107.8.

출처