Reacción #69003

Ecuación de reacción

2,6-difluoro-pyridin-3-ylamine

DMF

K2CO3

1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid

→

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

Rendimiento 13.0%

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
8. 8
   OtroThe resulting residue was purified by reverse phase chromatography

Procedimiento

To a suspension of 1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid (68 mg, 0.38 mmol) in CH2Cl2 (2 mL) was added 1-chloro-N,N-2-trimethylpropenylamine (50 μL, 0.38 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 (50 mg, 0.38 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 (53 mg, 0.38 mmol). The resulting mixture was heated by microwave to 150° C. for 10 min, after which the resulting mixture was filtered and concentrated. The resulting residue was purified by reverse phase chromatography affording 5-fluoro-2-(1-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-oxazolo[5,4-b]pyridine (13.1 mg, 0.049 mmol, 13% yield). ES MS (M+H+)=269; 1H NMR δ (ppm)(DMSO-d6): 9.07 (1H, d, J=2.12 Hz), 8.75 (1H, d, J=2.13 Hz), 8.42 (1H, t, J=7.74 Hz), 7.70 (1H, d, J=3.52 Hz), 7.29 (1H, d, J=8.41 Hz), 6.69 (1H, d, J=3.52 Hz), 3.89 (3H, s); HRMS m/z 269.0831 (C14H9FN4O+H+ requires 269.0833).

Fuente