Réaction #45417

Équation de réaction

NaCl

mixture

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

4-phenoxyphenylboronic acid

Na2CO3

→

desired product

Rendement 75.0%

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

Rendement 75.0%

Solvants

water

DMF

Conditions de réaction

Traitement

1. 1
   Extractionextracted with ethyl acetate (3×70 mL)
2. 2
   LavageThe combined organic extracts were washed with brine
3. 3
   Séchagedried (MgSO4)
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated 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
   Concentrationthe mixture was concentrated under vacuum
9. 9
   AutreThe residual silica gel with the absorbed crude product
10. 10
    Autrechromatographed (eluent 40% ethyl acetate/heptane)

Mode opératoire

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.

Source