Isopropyl iodide → HCID 57475958, compound

HRID 1994673Notes

Reaction equation

HRID 1994673 reaction equation
COC[N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[NH:13][S:14]([C:17]2[S:18][CH:19]=[CH:20][CH:21]=2)(=[O:16])=[O:15])[CH:6]=[C:5]1[C:22]([NH2:24])=[O:23].I[CH:26]([CH3:28])[CH3:27].C(=O)([O-])[O-].[K+].[K+].O.O.C(O)(=O)C(O)=O>C(OCC)(=O)C.[Cl-].[Na+].O.O.CO.CN(C)C(=O)C>[CH:26]([N:13]([S:14]([C:17]1[S:18][CH:19]=[CH:20][CH:21]=1)(=[O:15])=[O:16])[C:11]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:12]=1[NH:4][C:5]([C:22]([NH2:24])=[O:23])=[CH:6]2)([CH3:28])[CH3:27]

Participants

10

Reactant 4

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 61373Oxalic acid dihydrateHCID 57475954HCID 57475954, compound

Product 1

HCID 57475958HCID 57475958, compoundYield 34.2%

Reagents, catalysts & solvents 5

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of 1-(methoxymethyl)-7-[(2-thienylsulfonyl)amino]-1H-indole-2-carboxamide (1.0 g), 2-iodopropane (574 mg), potassium carbonate (1.13 g) and N,N-dimethylacetamide (5 ml) was stirred at room temperature for a week. The reaction mixture was diluted with ethyl acetate and saturated brine, and the organic layer was washed with aqueous sodium bicarbonate and saturated brine, dried over magnesium sulfate, and filtrated. The filtrate was concentrated, and the residue was subjected to basic silica gel column chromatography, and eluted with ethyl acetate-hexane (2:1) mixture to give a solid. A mixture of this solid, oxalic acid dihydrate (605 mg), methanol (15 ml) and water (15 ml) was stirred at 100° C. for 3.5 days. The reaction mixture was allowed to cool to room temperature, and the obtained solid was collected by filtration, washed successively with water, hexane-diisopropyl ether mixture and hexane. The obtained solid was subjected to basic silica gel column chromatography, and eluted with ethyl acetate-hexane mixture (2:1) to give the title compound (340 mg, yield 34%) as an amorphous solid.

Workup

  1. washthe organic layer was washed with aqueous sodium bicarbonate and saturated brine
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltrated
  4. concentrationThe filtrate was concentrated
  5. washeluted with ethyl acetate-hexane (2:1) mixture
  6. customto give a solid
  7. stirringwas stirred at 100° C. for 3.5 days
  8. temperatureto cool to room temperature
  9. filtrationthe obtained solid was collected by filtration
  10. washwashed successively with water, hexane-diisopropyl ether mixture and hexane
  11. washeluted with ethyl acetate-hexane mixture (2:1)

Sources & evidence

ORD record
ord-ee453959ac2040a7ac6441f2ff13af61
Source dataset
uspto-grants-2010_01
Patent number
US07652133B2

Reaction notes

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