Isopropyl iodide → HCID 57475958, compound

HRID 1851416Notes

Reaction equation

HRID 1851416 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+].C(=O)C=O>C(OCC)(=O)C.[Cl-].[Na+].O.CCCCCC.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

11

Reactant 4

HCID 6362Isopropyl iodideHCID 7860GlyoxalHCID 11430Potassium CarbonateHCID 57475954HCID 57475954, compound

Product 1

HCID 57475958HCID 57475958, compoundYield 34.2%

Reagents, catalysts & solvents 6

HCID 887MethanolSolventHCID 962WaterSolventHCID 8058HexaneSolventHCID 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 1 week. The reaction mixture was diluted with ethyl acetate and saturated brine. The organic layer was washed with aqueous sodium bicarbonate and saturated brine, dried over magnesium sulfate and filtrated. The filtrate was concentrated, subjected to NH silica gel column chromatography, and eluted with an ethyl acetate.hexane (2:1) mixture to give a solid. A mixture of this solid, oxalic acid dihydride (605 mg), methanol (15 mL) and water (15 mL) was stirred at 100° C. for 3.5 days. The reaction mixture was cooled to room temperature, and the obtained solid was collected by filtration, washed with water, a hexane. diisopropyl ether mixture and hexane in this order. The obtained solid was subjected to NH silica gel column chromatography, and eluted with an 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 an ethyl acetate
  6. customhexane (2:1) mixture to give a solid
  7. stirringwas stirred at 100° C. for 3.5 days
  8. temperatureThe reaction mixture was cooled to room temperature
  9. filtrationthe obtained solid was collected by filtration
  10. washwashed with water
  11. washeluted with an ethyl acetate

Sources & evidence

ORD record
ord-40f3d6446c944464a07553f1ff5094b6
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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