Réaction #2283871

Équation de réaction

5-Amino-7-azaindole

H2O

EDCI

HOBt

2,6-difluoro-3-nitrobenzoic acid

→

2,6-difluoro-5-nitro-(3H-imidazo[4,5-b]pyridin-6-yl)benzamide

Rendement 88.0%

Solvants

DMF

brine

Conditions de réaction

Traitement

1. 1
   Extractionextracted with EtOAc (2×)
2. 2
   Lavageextracts washed with water (1×)
3. 3
   Séchagedried over sodium sulfate
4. 4
   Concentrationconcentrated under reduced pressure
5. 5
   AutreThe resulting crude product was purified via silica gel chromatography

Mode opératoire

5-Amino-7-azaindole (820 mg, 6.2 mmol), 2,6-difluoro-3-nitrobenzoic acid (1200 mg, 6.2 mmol), EDCI (1200 mg, 6.2 mmol), and HOBt.H2O (930 mg, 6.2 mmol) were combined in dry DMF (20 mL) and stirred at room temperature for 16 hours. The reaction mixture was then diluted with brine, extracted with EtOAc (2×), extracts washed with water (1×), dried over sodium sulfate and concentrated under reduced pressure. The resulting crude product was purified via silica gel chromatography using an ISCO system (5% MeOH/DCM) to provide 2,6-difluoro-5-nitro-(3H-imidazo[4,5-b]pyridin-6-yl)benzamide (1.76 g, 88%). m/z (LC-MS) M+1=319.

Source