Diethyl Ether → HCID 59632563, compound

HRID 2369081Notes

Reaction equation

HRID 2369081 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[C:19]([F:22])([F:21])[F:20])[N:11]=[C:10](C(OC)=O)[CH:9]=2)=[CH:4][CH:3]=1.[CH3:27][Mg]Br.CC[O:32][CH2:33][CH3:34]>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[C:19]([F:21])([F:20])[F:22])[N:11]=[C:10]([C:33]([OH:32])([CH3:34])[CH3:27])[CH:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 59633348HCID 59633348, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 59632563HCID 59632563, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a suspension of methyl 5-(4-bromophenyl)-1-(2-(trifluoromethyl)phenyl)-1H-pyrazole-3-carboxylate (393 mg, 0.9 mmol) in dry toluene (9 mL) stirred at ambient temperature was added methylmagnesium bromide (1.4 mL of a 3.0M solution in ether, 4.2 mmol) dropwise. After 2¼ hours stirring at ambient temperature the reaction mixture was quenched by the addition of saturated ammonium chloride and EtOAc. The aqueous layer was extracted with EtOAc (3×). The combined organic extract were dried over Na2SO4, filtered and concentrated under reduced pressure to afford 2-(5-(4-bromophenyl)-1-(2-(trifluoromethyl)phenyl)-1H-pyrazol-3-yl)propan-2-ol as an orange-yellow oil, which was carried on to the subsequent step. GC/MS (EI, =426 [M+]

Workup

  1. stirringAfter 2¼ hours stirring at ambient temperature the reaction mixture
  2. customwas quenched by the addition of saturated ammonium chloride and EtOAc
  3. extractionThe aqueous layer was extracted with EtOAc (3×)
  4. extractionThe combined organic extract
  5. dry with materialwere dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-aa5108b7aec742cfb6c5851df262c874
Source dataset
uspto-grants-2014_04
Patent number
US08703805B2

Reaction notes

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