Potassium Carbonate → HCID 59240397, compound

HRID 1673007Notes

Reaction equation

HRID 1673007 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([OH:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[N:9]1.Br[CH2:19][C:20]([O:22][CH3:23])=[O:21].C([O-])([O-])=O.[K+].[K+]>C(#N)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([O:13][CH2:19][C:20]([O:22][CH3:23])=[O:21])=[CH:11][C:10]([C:14]([F:17])([F:15])[F:16])=[N:9]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 178516152HCID 178516152, compound

Product 1

HCID 59240397HCID 59240397, compoundYield 53.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 1-(2-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-ol (0.26 g, 1 mmol), methyl bromoacetate (0.195 mL, 2 mmol) and K2CO3 (276 mg, 2 mmol) in acetonitrile (2 mL) was shaken overnight at 85° C. After cooling, solid was removed by filtration and washed with acetonitrile. The filtrate was evaporated to give a crude, which was purified by chromatography on silica gel eluting with EtOAc-Hexane (1:4) to give methyl {[1-(2-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl]oxy}acetate (180 mg). 1H-NMR (CDCl3): δ 7.52 (2H, m), 7.42 (2H, m), 5.91 (1H, s), 4.67 (2H, s), 3.80 (3H, s). MS (ES): 335 [M+H]+

Workup

  1. temperatureAfter cooling
  2. customsolid was removed by filtration
  3. washwashed with acetonitrile
  4. customThe filtrate was evaporated
  5. customto give a crude, which
  6. customwas purified by chromatography on silica gel eluting with EtOAc-Hexane (1:4)

Sources & evidence

ORD record
ord-3b3ea94adf0049a291bdd18f2ebe27e3
Source dataset
uspto-grants-2011_08
Patent number
US07998995B2

Reaction notes

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