Reaction #1509641

Reaction equation

10

1-phenyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-benzo[d]imidazole

potassium acetate

→

Compound 28

Yield 81.0%

2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)benzo[d]oxazole

Yield 81.0%

Solvents

1,4-dioxane

Conditions

Workup

1. 1
   Otherwas degassed
2. 2
   TemperatureAfter cooling to room temperature
3. 3
   workup.ADDITIONthe mixture was poured into ethyl acetate (˜200 mL)
4. 4
   Filtrationfiltered
5. 5
   OtherThe filtrate was absorbed on silica gel
6. 6
   Otherpurified by column chromatography (hexanes/ethyl acetate, 4:1)

Procedure

A mixture of 10 (4.45 g, 16 mmol), bis(pinacolate)diborane (4.09 g, 16.1 mmol), anhydrous potassium acetate (3.14 g, 32 mmol) and Pd(dppf)Cl2 (0.48 g, 0.66 mmol) in anhydrous 1,4-dioxane (80 mL) was degassed and the resulting mixture was heated at about 85° C. for about 48 hours under argon. After cooling to room temperature, the mixture was poured into ethyl acetate (˜200 mL) and filtered. The filtrate was absorbed on silica gel and purified by column chromatography (hexanes/ethyl acetate, 4:1) to give a white solid (Compound 28) (4.15 g, in 81% yield).

Source