Reaction #1350574

Reaction equation

3-(3-aminophenyl)-4-bromo-1-methylpyrazole

triethylamine

4-trifluoromethoxyphenylacetic acid

HBTU

HOBT

→

title compound

Yield 68.0%

N-[3-(4-bromo-1-methylpyrazol-3-yl)phenyl]-2-[4-(trifluoromethoxy)phenyl]acetamide

Yield 68.0%

Solvents

DMF

DMF

Conditions

Workup

1. 1
   Otherquenched with aqueous sodium bicarbonate solution
2. 2
   workup.ADDITIONEthyl acetate was added
3. 3
   Otherthe organic phase separated
4. 4
   Washwashed with water (×3), brine
5. 5
   Dryingdried (MgSO4)
6. 6
   Otherevaporated

Procedure

A solution of 3-(3-aminophenyl)-4-bromo-1-methylpyrazole (35 mg, 0.14 mmol) and triethylamine (23 μL, 0.17 mmol) in DMF (0.5 mL) was added in one portion to a stirred solution of 4-trifluoromethoxyphenylacetic acid (31 mg, 0.14 mmol), HBTU (53 mg, 0.14 mmol) and HOBT (19 mg, 0.14 mmol) in DMF (1 mL). The mixture was heated at 70° C. for 24 h and then quenched with aqueous sodium bicarbonate solution. Ethyl acetate was added and the organic phase separated, washed with water (×3), brine, dried (MgSO4) and evaporated. Chromatography on flash silica (50% EtOAc/hexane) gave the title compound as a colourless solid (43 mg, 68%), m.p. 141.2-142.5° C. (EtOAc/hexane).

Source