Sodium Carbonate → HCID 89649473, compound

HRID 2207633Notes

Reaction equation

HRID 2207633 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13](Br)[CH:12]=[CH:11][C:10]=1[F:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:17][N:18]1[CH:22]=[C:21](B2OC(C)(C)C(C)(C)O2)[CH:20]=[N:19]1.C(=O)([O-])[O-].[Na+].[Na+].[OH-].[Na+]>CC#N.O.C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CCOC(C)=O>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([C:21]2[CH:20]=[N:19][N:18]([CH3:17])[CH:22]=2)[CH:12]=[CH:11][C:10]=1[F:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

9

Reactant 4

HCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 73553470HCID 73553470, compound

Product 1

HCID 89649473HCID 89649473, compoundYield 57.6%

Reagents, catalysts & solvents 4

HCID 178419050HCID 178419050, compoundCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 2-benzyloxy-4-bromo-1-fluoro-benzene [CAS: 1036724-54-5](1250 mg, 4.45 mmol) in MeCN (40 mL) and water (10 mL) was added 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1 h-pyrazole (925.18 mg, 4.45 mmol), sodium carbonate (1414.18 mg, 13.34 mmol) and bis(triphenylphosphine)palladium (II) dichloride (157.92 mg, 0.2200 mmol). The reaction was then heated at 100° C. for 4 hours. The reaction mixture was poured into EtOAc (100 mL) and aq NaOH (0.5M, 200 mL). The organics were separated, and washed with brine (75 mL), dried over MgSO4, filtered and concentrated in vacuo. The residue was then purified over silica (25 g, SNAP cartridge), eluting with between 0% and 40% EtOAc in isohexane. Fractions containing the desired product were combined and concentrated in vacuo to give 4-(3-benzyloxy-4-fluoro-phenyl)-1-methyl-pyrazole (D78) (760 mg, 2.5575 mmol, 57.6% yield) as a colourless oil;

Workup

  1. customThe organics were separated
  2. washwashed with brine (75 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was then purified over silica (25 g, SNAP cartridge)
  7. washeluting with between 0% and 40% EtOAc in isohexane
  8. additionFractions containing the desired product
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-21225710755b490680a1ae5a4d9f2c8d
Source dataset
uspto-grants-2016_06
Patent number
US09376436B2

Reaction notes

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