Sodium Carbonate → 4-Phenyl-1-(triphenylmethyl)-1H-pyrazole

HRID 1178107Notes

Reaction equation

HRID 1178107 reaction equation
C([O-])([O-])=O.[Na+].[Na+].I[C:8]1[CH:9]=[N:10][N:11]([C:13]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:12]=1.[C:32]1(B(O)O)[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>C1(C)C=CC=CC=1.O.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:32]1([C:8]2[CH:9]=[N:10][N:11]([C:13]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:12]=2)[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 153244794-Iodo-1-(triphenylmethyl)-1H-pyrazole

Product 1

HCID 595596204-Phenyl-1-(triphenylmethyl)-1H-pyrazoleYield 48.38%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 22272177Toluene waterSolvent

Procedure

Na2CO3 (146 mg, 1.37 mmol) was added to a stirred solution of 4-iodo-1-trityl-1H-pyrazole (300 mg, 0.69 mmol) in toluene: H2O (5:1, 11.5 mL). Pd (PPh3)4 (80 mg, 0.07 mmol) and phenylboronic acid (126 mg, 1.03 mmol) were then added and the reaction mixture was heated to reflux for 2 hrs. The reaction mixture was then diluted with water and the product was extracted with ethyl acetate. The organic layer was washed with saturated brine solution, dried over sodium sulphate and concentrated to get the residue. The residue obtained was purified by column chromatography (using silica gel of 60-120 mesh and 5% EtOAc in Hexane as eluent) afford 120 mg (48.38% yield) of 4-phenyl-1-trityl-1H-pyrazole. 1H NMR (CDCl3): δ 7.96-7.94 (s, 1H), 7.64-7.6 (s, 1H), 7.46-7.4 (d, 2H), 7.36-7.0 (m, 1H), 7.24-7.16 (m, 7H).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 2 hrs
  3. extractionthe product was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine solution
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated
  7. customto get the residue
  8. customThe residue obtained
  9. customwas purified by column chromatography (using silica gel of 60-120 mesh and 5% EtOAc in Hexane as eluent)

Sources & evidence

ORD record
ord-e1febe7ef4dd42d7bfefe2fe8e1ed167
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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