Acetic acid, 2-hydrazinyl-, ethyl ester → ethyl 2-(5-(5bromofuran-2-yl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetate

HRID 877452Notes

Reaction equation

HRID 877452 reaction equation
[Br:1][C:2]1[O:6][C:5]([C:7](=O)[CH2:8][C:9](=O)[C:10]([F:13])([F:12])[F:11])=[CH:4][CH:3]=1.[NH:16]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[NH2:17]>CO>[Br:1][C:2]1[O:6][C:5]([C:7]2[N:16]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[N:17]=[C:9]([C:10]([F:13])([F:12])[F:11])[CH:8]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 12509Acetic acid, 2-hydrazinyl-, ethyl esterHCID 897828761-(5-Bromofuran-2-yl)-4,4,4-trifluorobutane-1,3-dione

Product 1

HCID 89793128ethyl 2-(5-(5bromofuran-2-yl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetateYield 24%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of compound 44 (4 g, 14.0 mmol), ethyl 2-hydrazinylacetate (2.37 g, 15.0 mmol) and methanol (60 mL) was heated for 1.5 h. The reaction mixture was cooled to 0° C. and solvent was removed under reduced pressure. Water (100 mL) was added and the reaction mixture extracted with ethyl acetate (50 mL×3). Combined organic layer was washed with brine, dried over sodium sulphate and concentrated under reduced pressure. The crude compound was purified by column chromatography using 10% ethyl acetate in n-hexane as an eluent to afford the separated isomer 45 (1.2 g, 24%).

Workup

  1. temperaturewas heated for 1.5 h
  2. customsolvent was removed under reduced pressure
  3. additionWater (100 mL) was added
  4. extractionthe reaction mixture extracted with ethyl acetate (50 mL×3)
  5. washCombined organic layer was washed with brine
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated under reduced pressure
  8. customThe crude compound was purified by column chromatography

Sources & evidence

ORD record
ord-97b7a62642844ba889944e30fe4a7a0c
Source dataset
uspto-grants-2015_03
Patent number
US08987318B2

Reaction notes

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