Hydrochloric Acid → Methyl 3-[3-(4-trifluoromethoxy-phenyl)-pyrazol-1-yl]-benzoate

HRID 2172147Notes

Reaction equation

HRID 2172147 reaction equation
[F:1][C:2]([F:16])([F:15])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:14]=[CH:13][NH:12][N:11]=2)=[CH:6][CH:5]=1.[CH3:17][O:18][C:19]([C:21]1[CH:22]=[C:23](B(O)O)[CH:24]=[CH:25][CH:26]=1)=[O:20].N1C=CC=CC=1.Cl>CN(C)C=O.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[F:16][C:2]([F:1])([F:15])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:14]=[CH:13][N:12]([C:25]3[CH:26]=[C:21]([CH:22]=[CH:23][CH:24]=3)[C:19]([O:18][CH3:17])=[O:20])[N:11]=2)=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 27347143-(Methoxycarbonyl)benzeneboronic acidHCID 178506361HCID 178506361, compound

Product 1

HCID 66616070Methyl 3-[3-(4-trifluoromethoxy-phenyl)-pyrazol-1-yl]-benzoate

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 3-(4-trifluoromethoxy-phenyl)-1H-pyrazole (250 mg), 3-methoxycarbonylphenylboronic acid (540 mg) and pyridine (0.18 mL) in dimethylformamide (5 mL) is treated with copper (II) acetate (214 mg) and powdered activated 4 Å molecular sieves (0.5 g). The resulting mixture is heated to 60° C. for 16 h and cooled. The reaction mixture is poured into 1M aq. HCl (300 mL), and the resulting mixture is filtered through a glass microfiber filter pad. The pad is washed with ethyl acetate, and the filtrate is evaporated to afford the product, methyl 3-[3-(4-trifluoromethoxy-phenyl)-pyrazol-1-yl]-benzoate, as a solid (204 mg).

Workup

  1. temperaturecooled
  2. filtrationthe resulting mixture is filtered through a glass microfiber
  3. filtrationfilter pad
  4. washThe pad is washed with ethyl acetate
  5. customthe filtrate is evaporated

Sources & evidence

ORD record
ord-7b7ab0aa440d4ed2b8cc46cd18bc1079
Source dataset
uspto-grants-2015_06
Patent number
US09051342B2

Reaction notes

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