Reaktion #1715264

Reaktionsgleichung

3-bromo-1-methyl-6-tosyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazine

4-formylphenylboronic acid

EtOH

Cs2CO3

→

title compound

Ausbeute 76.2%

4-(1-Methyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-3-yl)benzaldehyde

Ausbeute 76.2%

Lösungsmittel

1,4-dioxane

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeTo a microwave reaction
2. 2
   FiltrationThe mixture was filtered through a filtration tube with a polyethylene frit
3. 3
   Waschenthe resulting solid was rinsed with EtOAc (5 mL)
4. 4
   workup.DISSOLUTIONThe solid was dissolved in a 9:1 DCM/MeOH solution
5. 5
   Filtrationfiltered
6. 6
   EinengenThe filtrate was concentrated under reduced pressure
7. 7
   Sonstigeby drying overnight in a vacuum oven at about 65° C.

Vorschrift

To a microwave reaction vial containing 3-bromo-1-methyl-6-tosyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazine (0.100 g, 0.247 mmol, Preparation #AB.1), 4-formylphenylboronic acid (0.074 g, 0.493 mmol, Lancaster) and SiliaCat® DPP-Pd (0.031 g, 0.025 mmol, Silicycle) in 1,4-dioxane (1.0 mL) and EtOH (1.0 mL) was added a solution of Cs2CO3 (0.177 g, 0.543 mmol) in water (0.3 mL). The mixture was heated in a microwave at 150° C. for 30 min. The mixture was filtered through a filtration tube with a polyethylene frit, and the resulting solid was rinsed with EtOAc (5 mL). The solid was dissolved in a 9:1 DCM/MeOH solution and filtered. The filtrate was concentrated under reduced pressure followed by drying overnight in a vacuum oven at about 65° C. to give the title compound (0.052 g, 76%): LC/MS (Table 2, Method c) Rf=1.67 min.; MS m/z: 277 (M+H)+.

Quelle