Sodium Iodide → HCID 66955311, compound

HRID 1697879Notes

Reaction equation

HRID 1697879 reaction equation
[CH3:1][C:2]1[NH:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][C:10]([CH3:13])=[C:9]([N+:14]([O-:16])=[O:15])[CH:8]=2)[CH:3]=1.[Si:17](Br)([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18].C([O-])([O-])=O.[Cs+].[Cs+].[Na+].[I-].CN1[C:38](=[O:39])[CH2:37]CC1>CCOC(C)=O>[C:20]([Si:17]([CH3:19])([CH3:18])[O:39][CH2:38][CH2:37][N:6]1[C:2]([CH3:1])=[CH:3][C:4]([C:7]2[CH:12]=[CH:11][C:10]([CH3:13])=[C:9]([N+:14]([O-:16])=[O:15])[CH:8]=2)=[N:5]1)([CH3:23])([CH3:22])[CH3:21]

Participants

7

Reactant 5

HCID 5238Sodium IodideHCID 10796Cesium carbonateHCID 13387N-methyl-2-pyrrolidoneHCID 586375Silane, bromo(1,1-dimethylethyl)dimethyl-HCID 593775315-methyl-3-(4-methyl-3-nitro-phenyl)-1H-pyrazole

Product 1

HCID 66955311HCID 66955311, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 5-Methyl-3-(4-methyl-3-nitro-phenyl)-1H-pyrazole, tert-butyl-dimethylsilyl bromide, Cs2CO3 and NaI in NMP was heated in a microwave oven at 100° C. for 1 hour, and then cooled to room temperature. The reaction mixture was diluted with EtOAc, washed with water and brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by “flash chromatography” (0 to 30% EtOAc in hexanes to give 867 mg of 1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-methyl-3-(4-methyl-3-nitro-phenyl)-1H-pyrazole as an oil that also contained 1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-methyl-5-(4-methyl-3-nitro-phenyl)-1H-pyrazole as a minor product.

Workup

  1. washwashed with water and brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by “flash chromatography” (0 to 30% EtOAc in hexanes

Sources & evidence

ORD record
ord-1c9f760ceda04b98bd92d2452c3fb0b3
Source dataset
uspto-grants-2012_04
Patent number
US08163929B2

Reaction notes

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