Reaction #92470

Reaction equation

N-(5-(5-ethynyl-1H-benzo[d]imidazol-1-yl)-2′,4′-difluorobiphenyl-3-yl)acetamide

ethyl-2-azidoacetate

sodium ascorbate

→

Ethyl 2-(5-(1-(5-acetamido-2′,4′-difluoro-[1,1′-biphenyl]-3-yl)-1H-benzo[d]-imidazol-5-yl)-1H-1,2,3-triazol-1-yl)acetate

Yield 75.0%

Solvents

t-butanol

water

Conditions

Workup

1. 1
   OtherThe mixture was quenched with water
2. 2
   Otherthe precipitate formed
3. 3
   Filtrationwas filtered
4. 4
   Otherdried
5. 5
   Otherto give the product in 75% yield (250 mg)

Procedure

A mixture of N-(5-(5-ethynyl-1H-benzo[d]imidazol-1-yl)-2′,4′-difluorobiphenyl-3-yl)acetamide (258 mg, 0.6 mmol), ethyl-2-azidoacetate (180 mg, 0.8 mmol, 1.3 eq.), sodium ascorbate (125 mg, 0.6 mmol, 1.0 eq.) and copper sulfate pentahydrate (80 mg, 0.32 mmol, 0.5 eq.) in t-butanol and water (1:1, 3 ml) was stirred for 12 h at RT. The mixture was quenched with water and the precipitate formed was filtered and dried to give the product in 75% yield (250 mg).

Source