Reaktion #91876

Reaktionsgleichung

3-phenyl-5-bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

2-methoxy-benzene boronic acid

K2CO3

→

3-phenyl-5-(4-methoxyphenyl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

Ausbeute 98.0%

Lösungsmittel

toluene ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture is cooled to room temperature
2. 2
   Einengenconcentrated under a vacuum
3. 3
   workup.DISSOLUTIONredissolved in a water/CH2Cl2 mixture
4. 4
   ExtraktionThe aqueous phase is extracted several times with CH2Cl2
5. 5
   Sonstigethe combined organic phases are dried on MgSO4
6. 6
   SonstigeThe solvent is evaporated under reduced pressure
7. 7
   Sonstigethe residue purified by flash chromatography on silica gel (100% CH2Cl2)
8. 8
   Sonstigeto yield the purified product in the form of a colorless oil with a yield of 98%

Vorschrift

To a solution of 3-phenyl-5-bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (309 mg, 0.75 mmol) in a 3:1 toluene/ethanol mixture (24 ml) are added 2-methoxy-benzene boronic acid (125 mg, 0.83 mmol), K2CO3 (2.4 ml of 2 M solution in water, 4.5 mmol), Pd(PPh3)4 (1.5 mol %), and the mixture is heated at 85° C. for 2 hours under argon. The mixture is cooled to room temperature, concentrated under a vacuum and redissolved in a water/CH2Cl2 mixture. The aqueous phase is extracted several times with CH2Cl2 and the combined organic phases are dried on MgSO4. The solvent is evaporated under reduced pressure and the residue purified by flash chromatography on silica gel (100% CH2Cl2) to yield the purified product in the form of a colorless oil with a yield of 98%.

Quelle