Reacción #2292779

Ecuación de reacción

NaHCO3

potassium 2-methylpropan-2-olate

(S)-tert-butyl methyl(pyrrolidin-3-yl)carbamate

(S)-1-(6-bromo-1-methyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethanamine

→

title compound

Rendimiento 49.3%

tert-Butyl ((S)-1-(5-((S)-1-aminoethyl)-1-methyl-1H-pyrrolo[3,2-b]pyridin-6-yl)pyrrolidin-3-yl)(methyl)carbamate

Rendimiento 49.3%

Disolventes

dioxane

EtOAc

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroAfter evacuating the flask
2. 2
   Otroflushing it with nitrogen
3. 3
   TemperaturaAfter cooling
4. 4
   Secadodried over MgSO4
5. 5
   Filtraciónfiltered
6. 6
   Concentraciónconcentrated in vacuo
7. 7
   OtroThe crude product was purified by preparative HPLC (acid mode, 25-50% ACN/water)
8. 8
   Concentraciónconcentrated in vacuo
9. 9
   Otroto remove ACN
10. 10
    Extracciónextracted with EtOAc
11. 11
    Secadodried over MgSO4
12. 12
    Filtraciónfiltered
13. 13
    Concentraciónconcentrated in vacuo

Procedimiento

To a 50 mL pear flask were added (S)-tert-butyl methyl(pyrrolidin-3-yl)carbamate (235 mg, 1.173 mmol) and (S)-1-(6-bromo-1-methyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethanamine (166 mg, 0.652 mmol). After evacuating the flask and flushing it with nitrogen, the flask was charged with dioxane (1.7 mL) and potassium 2-methylpropan-2-olate (1.0 M in THF, 1.4 mL, 1.4 mmol). The mixture was then heated to 90° C. for 1 hour. After cooling, the mixture was worked up with saturated NaHCO3 and EtOAc. The organic layers were combined, dried over MgSO4, filtered, and concentrated in vacuo. The crude product was purified by preparative HPLC (acid mode, 25-50% ACN/water). The product-containing fractions were neutralized with a small amount of saturated NaHCO3, concentrated in vacuo to remove ACN, and then extracted with EtOAc. The organic layers were combined, dried over MgSO4, filtered, and concentrated in vacuo to give the title compound (120 mg, 49.0%). ESI-MS m/z [M+H]+ calc'd for C20H31N5O2, 374. found 374.

Fuente