Pyridine → Ethyl 3-(1,1-dimethylethyl)-1-(3-fluorophenyl)-1H-pyrazole-5-carboxylate

HRID 1930327Notes

Reaction equation

HRID 1930327 reaction equation
[F:1][C:2]1[CH:3]=[C:4](B(O)O)[CH:5]=[CH:6][CH:7]=1.[C:11]([C:15]1[CH:19]=[C:18]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[NH:17][N:16]=1)([CH3:14])([CH3:13])[CH3:12].N1C=CC=CC=1>C(Cl)Cl.CCOC(C)=O.CC([O-])=O.CC([O-])=O.[Cu+2]>[C:11]([C:15]1[CH:19]=[C:18]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[N:17]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=2)[N:16]=1)([CH3:14])([CH3:12])[CH3:13]

Participants

7

Reactant 3

HCID 1049PyridineHCID 27339863-Fluorophenylboronic acidHCID 2743509Ethyl 3-tert-butyl-1H-pyrazole-5-carboxylate

Product 1

HCID 69042455Ethyl 3-(1,1-dimethylethyl)-1-(3-fluorophenyl)-1H-pyrazole-5-carboxylateYield 54.1%

Reagents, catalysts & solvents 3

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-Fluorophenylboronic acid (0.70 g, 5.0 mmol), ethyl 3-tert-butyl-1H-pyrazole-5-carboxylate (0.981 g, 5.0 mmol), Cu(OAc)2 (0.908 g, 5.0 mmol), pyridine (2.45 ml, 30 mmol) and 4A MS (1.9 g) were combined in CH2Cl2 (48 ml) and stirred open to air at RT for 4 d. The reaction mixture was diluted with EtOAc (150 mL), washed with 3M HCl (2×50 mL), H2O (50 mL) and brine (50 mL), dried (MgSO4) and concentrated in vacuo. The crude product was purified by chromatography to afford ethyl 3-tert-butyl-1-(3-fluorophenyl)-1H-pyrazole-5-carboxylate (0.786 g, 54% yield) as colorless oil. MS (ESI) m/z: 291 (M+H+).

Workup

  1. washwashed with 3M HCl (2×50 mL), H2O (50 mL) and brine (50 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by chromatography

Sources & evidence

ORD record
ord-937a4cb5c5614dcf843e94eae86e6ddd
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

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