Dimethylformamide → HCID 57442277, compound

HRID 2079917Notes

Reaction equation

HRID 2079917 reaction equation
[CH2:1]([C:3]1[NH:4][C:5]2[C:10]([C:11]=1[I:12])=[CH:9][CH:8]=[C:7]([N+:13]([O-:15])=[O:14])[CH:6]=2)[CH3:2].CN(C=O)C.[CH2:21](I)[CH3:22]>C(OCC)(=O)C>[CH2:21]([N:4]1[C:5]2[C:10](=[CH:9][CH:8]=[C:7]([N+:13]([O-:15])=[O:14])[CH:6]=2)[C:11]([I:12])=[C:3]1[CH2:1][CH3:2])[CH3:22]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 6340IodoethaneHCID 57442278HCID 57442278, compound

Product 1

HCID 57442277HCID 57442277, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Add to a solution of 2-ethyl-3-iodo-6-nitro-1H-indole (0.30 g, 00.95 mmol) in anhydrous DMF (5 mL) sodium hexamethyldisilylamide (1.0M in THF, 1.0 mL, 1.00 mmol) dropwise followed by ethyl iodide (0.23 mL, 2.85 mmol) and stir 3 hours at ambient temperature. Quench the reaction with 1N HCl and add ethyl acetate. Wash the organic layer 2×1N HCl, 1× brine. Dry the organic layer over sodium sulfate, concentrate in vacuo, and flash chromatograph with 20% ethyl acetate hexane to afford 0.28 g (86%) of the title compound.

Workup

  1. customQuench
  2. customthe reaction with 1N HCl
  3. washWash the organic layer 2×1N HCl, 1× brine
  4. dry with materialDry the organic layer over sodium sulfate
  5. concentrationconcentrate in vacuo, and flash chromatograph with 20% ethyl acetate hexane

Sources & evidence

ORD record
ord-b806d15cbfa44d64b9160942cc8d02b7
Source dataset
uspto-grants-2011_04
Patent number
US07932284B2

Reaction notes

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