Ethyl 4,4,4-trifluoroacetoacetate → HCID 136376523, compound

HRID 402464Notes

Reaction equation

HRID 402464 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:12]=[C:11]([NH2:13])[N:10]([CH3:14])[N:9]=1.C([O:17][C:18](=O)[CH2:19][C:20](=O)[C:21]([F:24])([F:23])[F:22])C>C(O)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:12]2[C:20]([C:21]([F:24])([F:23])[F:22])=[CH:19][C:18](=[O:17])[NH:13][C:11]=2[N:10]([CH3:14])[N:9]=1

Participants

4

Reactant 2

HCID 67793Ethyl 4,4,4-trifluoroacetoacetateHCID 33783247HCID 33783247, compound

Product 1

HCID 136376523HCID 136376523, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 3-(2-fluorophenyl)-1-methyl-1H-pyrazol-5-amine (830 mg, 4.34 mmol) and 4,4,4-Trifluoro-3-oxo-butyric acid ethyl ester (960 mg, 5.21 mmol) in acetic acid (5 ml) was irradiated using a microwave at 150° C. for 1.5 h. After completion of the reaction, ice-cold water was added and the reaction mixture was stirred for 10 min. The precipitate was filtered, washed twice with pentane and dried under vacuum to yield 900 mg (67%) of the title compound. [1H-NMR (CDCl3, 300 MHz): δ 13.6 (s, 1H), 7.51-7.05 (m, 4H), 6.75 (s, 1H), 4.21 (s, 3H); LCMS RtA=1.459 min; [M+H]+=312.1]

Workup

  1. customat 150° C.
  2. customfor 1.5 h
  3. customAfter completion of the reaction, ice-cold water
  4. additionwas added
  5. filtrationThe precipitate was filtered
  6. washwashed twice with pentane
  7. customdried under vacuum

Sources & evidence

ORD record
ord-4e57a670e11c454abd7be90f5339cdae
Source dataset
uspto-grants-2014_06
Patent number
US08742106B2

Reaction notes

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