Hydrochloric Acid → 1-(2-Benzyloxy-5-bromo-benzyl)-5-Trifluoromethyl-1H-pyrazole-3-carboxylic acid ethyl ester

HRID 1053993Notes

Reaction equation

HRID 1053993 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[NH:8][N:7]=1)=[O:5])[CH3:2].[CH2:15]([O:22][C:23]1[CH:28]=[CH:27][C:26]([Br:29])=[CH:25][C:24]=1[CH2:30]Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C([O-])([O-])=O.[K+].[K+].Cl>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[C:9]([C:11]([F:13])([F:14])[F:12])[N:8]([CH2:30][C:24]2[CH:25]=[C:26]([Br:29])[CH:27]=[CH:28][C:23]=2[O:22][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:7]=1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 27269191H-Pyrazole-3-carboxylic acid, 5-(trifluoromethyl)-, ethyl esterHCID 117832201-(Benzyloxy)-4-bromo-2-(bromomethyl)benzene

Product 1

HCID 866856941-(2-Benzyloxy-5-bromo-benzyl)-5-Trifluoromethyl-1H-pyrazole-3-carboxylic acid ethyl esterYield 67.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-trifluoromethyl-1H-pyrazole-3-carboxylic acid ethyl ester (0.114 g, 0.55 mmol) and 1-benzyloxy-4-bromo-2-bromomethyl-benzene (0.196 g, 0.55 mmol) in DMF (2 ml) cooled at RT under N2 atmosphere was added K2CO3 (0.19 g, 1.375 mmol) The mixture was stirred at RT overnight, then acidified with HCl (2M, aq.) and extracted with EtOAc. The organic layer was separated, washed with brine, dried (MgSO4) and evaporated to dryness. The residue was purified by MPLC (10 g SiO2 cartridge, eluent 90% iso-hexane-10% EtOAc) yielding 0.18 g of title compound.

Workup

  1. extractionextracted with EtOAc
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated to dryness
  6. customThe residue was purified by MPLC (10 g SiO2 cartridge, eluent 90% iso-hexane-10% EtOAc)

Sources & evidence

ORD record
ord-710dcf2459bf4c22b1131f8e708285ec
Source dataset
uspto-grants-2016_07
Patent number
US09394284B2

Reaction notes

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