Sodium Carbonate → 1-(4'-Nitrophenyl)-5-(4-methoxyphenyl)-3-methylpyrazole

HRID 1634099Notes

Reaction equation

HRID 1634099 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:14](Br)=[CH:13][C:12]([CH3:16])=[N:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1.C([O-])([O-])=O.[Na+].[Na+]>C1COCC1.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>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:14]([C:22]3[CH:23]=[CH:24][C:19]([O:18][CH3:17])=[CH:20][CH:21]=3)=[CH:13][C:12]([CH3:16])=[N:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 114829301-(4'-Nitrophenyl)-5-bromo-3-methylpyrazole

Product 1

HCID 155056401-(4'-Nitrophenyl)-5-(4-methoxyphenyl)-3-methylpyrazoleYield 94.2%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(4′-nitrophenyl)-5-bromo-3-methylpyrazole (100 mg, 0.35 mmol) in THF (5 mL) was added Pd(PPh3)4 (20 mg, 0.017 mmol) and 4-methoxyphenylboronic acid (60 mg, 0.39 mmol), followed by 2 M Na2CO3 (0.35 mL, 0.70 mmol). The mixture was heated to reflux for 4 hr, and was then quenched with water and extracted with EtOAc. The extract was dried over MgSO4 and concentrated. The residue was purified by column chromatography on silica gel (hexane/acetate, 15:1) to give the title compound (102 mg, 94%). mp: 155-158° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 4 hr
  3. customwas then quenched with water
  4. extractionextracted with EtOAc
  5. dry with materialThe extract was dried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on silica gel (hexane/acetate, 15:1)

Sources & evidence

ORD record
ord-9e245a3c13eb4e2c85650250e91dae09
Source dataset
uspto-grants-2003_01
Patent number
US06506747B1

Reaction notes

Loading…