Diiodomethane → HCID 66720670, compound

HRID 1639766

Reaction equation

HRID 1639766 reaction equation
[CH3:1][N:2]1[CH:10]=[C:9]2[C:4]([CH:5]=[CH:6][CH:7]=[C:8]2/[CH:11]=[CH:12]\[CH2:13][OH:14])=[N:3]1.[CH3:15]CCCCC.C([Zn]CC)C.ICI>C(Cl)Cl.[Cl-].[NH4+].O>[CH3:1][N:2]1[CH:10]=[C:9]2[C:4]([CH:5]=[CH:6][CH:7]=[C:8]2[C@H:11]2[CH2:15][C@H:12]2[CH2:13][OH:14])=[N:3]1

Participants

7

Reactant 3

HCID 6346DiiodomethaneHCID 59334468(2Z)-3-(2-methyl-2H-indazol-4-yl)prop-2-en-1-olHCID 178443585HCID 178443585, compound

Product 1

HCID 66720670HCID 66720670, compoundYield 63%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 25517Ammonium ChlorideSolvent

Procedure

Under argon gas atmosphere, to a suspension of (2Z)-3-(2-methyl-2H-indazol-4-yl)prop-2-en-1-ol (60.0 mg, 0.319 mmol) in methylene chloride (3 mL) was added 1 M diethylzinc hexane solution (1.60 mL, 1.60 mmol) under ice-cooling and the mixture was stirred for 10 min. Diiodomethane (128 μL, 1.59 mmol) was added, and the mixture was stirred at room temperature for 2 hr. The reaction solution was diluted with saturated aqueous ammonium chloride solution and water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (methanol/ethyl acetate=0/100→5/95) to give the title compound (40.5 mg, yield 63%).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 2 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (methanol/ethyl acetate=0/100→5/95)

Sources & evidence

ORD record
ord-f639fd6103aa4376851aded75d28d9ae
Source dataset
uspto-grants-2012_02
Patent number
US08110585B2

Linked notes

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