Iodine → HCID 67778921, compound

HRID 1026307Notes

Reaction equation

HRID 1026307 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[CH:8][C:9]3[C:13]([CH:14]=2)=[N:12][N:11]([C:15]2[CH:20]=[CH:19][C:18]([O:21][Si:22]([CH:29]([CH3:31])[CH3:30])([CH:26]([CH3:28])[CH3:27])[CH:23]([CH3:25])[CH3:24])=[CH:17][CH:16]=2)[CH:10]=3)[CH2:3][CH2:2]1.C([N-]C(C)C)(C)C.[Li+].[I:40]I.S([O-])([O-])(=O)=S.[Na+].[Na+]>C1COCC1>[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[CH:8][C:9]3[C:13]([CH:14]=2)=[N:12][N:11]([C:15]2[CH:20]=[CH:19][C:18]([O:21][Si:22]([CH:26]([CH3:28])[CH3:27])([CH:23]([CH3:25])[CH3:24])[CH:29]([CH3:31])[CH3:30])=[CH:17][CH:16]=2)[C:10]=3[I:40])[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 807IodineHCID 24477Sodium ThiosulfateHCID 2724682Lithium diisopropylamideHCID 67777605HCID 67777605, compound

Product 1

HCID 67778921HCID 67778921, compoundYield 75.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

To a solution of 6-(cyclopropylmethoxy)-2-(4-{[tris(1-methylethyl)silyl]oxy}phenyl)-2H-indazole (803 mg) in THF (6 mL) was added dropwise a THF solution (1.11 M, 3.3 mL) of lithiumdiisopropylamide at −78° C. under an argon atmosphere, and the mixture was stirred at 0° C. for 2 hr. To the reaction mixture was added a solution of iodine (933 mg) in THF (3 mL), and the mixture was stirred at 0° C. for 1 hr. To the reaction mixture was added saturated aqueous sodium thiosulfate solution, and the mixture was extracted twice with ethyl acetate. The combined organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained crystals were recrystallized from methanol to give the title compound as colorless crystals (782 mg).

Workup

  1. stirringthe mixture was stirred at 0° C. for 1 hr
  2. extractionthe mixture was extracted twice with ethyl acetate
  3. washThe combined organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained crystals were recrystallized from methanol

Sources & evidence

ORD record
ord-0f73ecde071c40e792b6531b453d9cbd
Source dataset
uspto-grants-2014_05
Patent number
US08729102B2

Reaction notes

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