Reaction #44272

Reaction equation

6-bromo-1-(2,3-dihydro-benzofuran-5-ylmethyl)-1H-[1,2,3]triazolo[4,5-b]pyrazine

1-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole

sodium carbonate

N2

→

1-(2,3-dihydro-benzofuran-5-ylmethyl)-6-(1-methyl-1H-pyrazol-4-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazine

Yield 24.0%

Solvents

DME water

Conditions

Workup

1. 1
   OtherThe reaction solution was degassed with N2 again
2. 2
   FiltrationThe reaction mixture was filtered through celite,
3. 3
   Concentrationconcentrated
4. 4
   Otherpurified with a reverse-phased preparative HPLC
5. 5
   Washeluting with acetonitrile-water having 0.1% acetic acid

Procedure

To a solution of 6-bromo-1-(2,3-dihydro-benzofuran-5-ylmethyl)-1H-[1,2,3]triazolo[4,5-b]pyrazine (50 mg, 0.15 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (34 mg, 0.165 mmol), and sodium carbonate (48 mg, 0.45 mmol) in DME/water (4 mL/1 mL) degassed with N2 was added Pd(PPh3)2Cl2 (5 mg, 0.008 mmol). The reaction solution was degassed with N2 again and stirred for 16 hours at 80° C. The reaction mixture was filtered through celite, concentrated, and purified with a reverse-phased preparative HPLC eluting with acetonitrile-water having 0.1% acetic acid to give 1-(2,3-dihydro-benzofuran-5-ylmethyl)-6-(1-methyl-1H-pyrazol-4-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazine (12 mg, 24% yield).

Source