Iodine → HCID 68441206, compound

HRID 1592821Notes

Reaction equation

HRID 1592821 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[Mg].II.C([O:20][C:21]1[C:25]([CH:26]=O)=[C:24]([CH3:28])[N:23]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[N:22]=1)C1C=CC=CC=1.[Cl-].[NH4+]>O1CCCC1>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([CH2:26][C:25]2[C:21](=[O:20])[NH:22][N:23]([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[C:24]=2[CH3:28])=[CH:3][CH:4]=1

Participants

7

Reactant 5

HCID 807IodineHCID 77304-BromoanisoleHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 17863259HCID 17863259, compound

Product 1

HCID 68441206HCID 68441206, compoundYield 51.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A Grignard reagent was prepared from 4-bromoanisole (1.2 g), magnesium (0.16 g), a catalytic amount of iodine and tetrahydrofuran (20 mL) in the usual manner. To the obtained Grignard reagent solution was added a solution of 3-benzyloxy-4-formyl-5-methyl-1-phenyl-1H-pyrazole(1.5 g) in tetrahydrofuran (15 mL) at 0° C., and the mixture was stirred for 30 minutes. To the reaction mixture was added a saturated aqueous ammonium chloride solution, and the mixture was extracted with diethyl ether. The organic layer was washed with brine and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was dissolved in methanol (50 mL) and tetrahydrofuran (50 mL). To the solution was added 10% palladium-carbon powder, and the mixture was stirred at room temperature under a hydrogen atmosphere overnight. Insoluble materials were removed by filtration, and the solvent of the filtrate was removed under reduced pressure. To the residue was added ethanol, and the precipitates was collected by filtration, washed with ethanol and hexane, and dried under reduced pressure to give the title compound (0.78 g).

Workup

  1. extractionthe mixture was extracted with diethyl ether
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was removed under reduced pressure
  5. dissolutionThe residue was dissolved in methanol (50 mL)
  6. additionTo the solution was added 10% palladium-carbon powder
  7. stirringthe mixture was stirred at room temperature under a hydrogen atmosphere overnight
  8. customInsoluble materials were removed by filtration
  9. customthe solvent of the filtrate was removed under reduced pressure
  10. additionTo the residue was added ethanol
  11. filtrationthe precipitates was collected by filtration
  12. washwashed with ethanol and hexane
  13. customdried under reduced pressure

Sources & evidence

ORD record
ord-bc6878dac9ea412990a2d19db5cc0b9c
Source dataset
uspto-grants-2007_11
Patent number
US07294618B2

Reaction notes

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