Pivalic acid → HCID 66863438, compound

HRID 1466596Notes

Reaction equation

HRID 1466596 reaction equation
[CH2:1]([N:6]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[N:7]1)[CH2:2][CH:3]([CH3:5])[CH3:4].Br[C:15]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=1[O:22][CH3:23].C(=O)([O-])[O-].[K+].[K+].CC(C)(C)C(O)=O>CN(C)C(=O)C.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:21][C:19]1[CH:18]=[CH:17][C:16]([O:22][CH3:23])=[C:15]([C:10]2[N:6]([CH2:1][CH2:2][CH:3]([CH3:5])[CH3:4])[N:7]=[CH:8][C:9]=2[N+:11]([O-:13])=[O:12])[CH:20]=1

Participants

8

Reactant 4

HCID 6417Pivalic acidHCID 11430Potassium CarbonateHCID 5219352-Bromo-4-chloroanisoleHCID 66847207HCID 66847207, compound

Product 1

HCID 66863438HCID 66863438, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 1-Isopentyl-4-nitro-1H-pyrazole (356.9 mg, 1.95 mmol, 1.00 eq), 2-Bromo-4-chloroanisole (0.37 ml, 2.72 mmol, 1.40 eq), Palladium (II) acetate (88 mg, 0.39 mmol, 0.20 eq), Di(1-adanmtyl)-n-butylphosphine (209 mg, 0.58 mmol, 0.30 eq), potassium carbonate (807 mg, 5.84 mmol, 3.00 eq) and trimethylacetic acid (52 mg, 0.50 mmol, 0.26 eq) in 5.0 mL N,N-Dimethylacetamide was stirred at 120° C. for 12 hours. The reaction mixture was cooled to room temperature and diluted with 20 mL ethyl acetate and filtered. The filtrate was then concentrated and used as is for the next step. LCMS (ESI) m+H=324.3

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered
  3. concentrationThe filtrate was then concentrated

Sources & evidence

ORD record
ord-57fb71f4efb94be6811d9b660e9a64a7
Source dataset
uspto-grants-2015_04
Patent number
US08999998B2

Reaction notes

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