Reacción #68999

Ecuación de reacción

DMF

K2CO3

2,6-difluoro-pyridin-3-ylamine

1-(4-methoxy-benzyl)-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid

→

5-fluoro-2-[1-(4-methoxy-benzyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-oxazolo[5,4-b]pyridine

Disolventes

pyridine

CH2Cl2

Condiciones de reacción

Tratamiento posterior

1. 1
   Concentraciónthe reaction mixture was concentrated
2. 2
   Otroaffording a residue that
3. 3
   workup.ADDITIONwas added in one portion
4. 4
   ConcentraciónAfter an additional 30 minutes the reaction mixture was concentrated to dryness
5. 5
   Otroaffording a residue
6. 6
   Filtraciónafter which the resulting mixture was filtered
7. 7
   Concentraciónconcentrated

Procedimiento

To a stirred solution of 1-(4-methoxy-benzyl)-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid (47 mg, 0.17 mmol) in CH2Cl2 (2 mL) was added 1-chloro-N,N-2-trimethylpropenylamine (45 μL, 0.34 mmol). Following formation of the resulting acid chloride, the reaction mixture was concentrated affording a residue that was dissolved in pyridine (2 mL) before 2,6-difluoro-pyridin-3-ylamine (20 mg, 0.15 mmol) was added in one portion. After an additional 30 minutes the reaction mixture was concentrated to dryness affording a residue, to which was added DMF (2 mL) and K2CO3 (64 mg, 0.46 mmol). The resulting mixture was heated by microwave to 150° C. for 10 min, after which the resulting mixture was filtered and concentrated, affording 5-fluoro-2-[1-(4-methoxy-benzyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-oxazolo[5,4-b]pyridine as a crude residue which was subsequently used without further purification. ES MS (M+H+)=375.

Fuente