Sodium Carbonate → tert-butyl[4-(4-bromo-2-fluorophenyl)-1H-pyrazol-1-yl]acetate

HRID 1257854Notes

Reaction equation

HRID 1257854 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](I)=[C:4]([F:9])[CH:3]=1.[C:10]([O:14][C:15](=[O:31])[CH2:16][N:17]1[CH:21]=[C:20](B2OC(C)(C)C(C)(C)O2)[CH:19]=[N:18]1)([CH3:13])([CH3:12])[CH3:11].C(=O)([O-])[O-].[Na+].[Na+]>C1COCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:10]([O:14][C:15](=[O:31])[CH2:16][N:17]1[CH:21]=[C:20]([C:5]2[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][C:4]=2[F:9])[CH:19]=[N:18]1)([CH3:13])([CH3:11])[CH3:12]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 27245164-Bromo-2-fluoro-1-iodobenzeneHCID 59216326tert-Butyl 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)acetate

Product 1

HCID 86654279tert-butyl[4-(4-bromo-2-fluorophenyl)-1H-pyrazol-1-yl]acetate

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4-bromo-2-fluoro-1-iodobenzene (380 mg, 1.3 mmol) in THF (10 mL) was added tert-butyl[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]acetate (390 mg, 1.3 mmol), 2M sodium carbonate in water (2.5 mL) and tetrakis(triphenylphosphine)palladium (40 mg, 0.04 mmol). The solution was degassed with N2, and heated at 80° C. overnight. The mixture was cooled to RT, poured into water, extracted with EtOAc, washed with brine, dried over MgSO4, filtered, and concentrated. The residue was purified by flash chromatograph on a silica gel column with EtOAc in Hexanes (30%) to afford the desired compound. LCMS: (M+57)=299.0.

Workup

  1. customThe solution was degassed with N2
  2. temperatureThe mixture was cooled to RT
  3. additionpoured into water
  4. extractionextracted with EtOAc
  5. washwashed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by flash chromatograph on a silica gel column with EtOAc in Hexanes (30%)

Sources & evidence

ORD record
ord-1d0fc036c0bf49c5bb034566b1363dc9
Source dataset
uspto-grants-2013_06
Patent number
US08461330B2

Reaction notes

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