Methyl iodide → HCID 67273994, compound

HRID 1696753Notes

Reaction equation

HRID 1696753 reaction equation
[H-].[Na+].[CH3:3][O:4][CH2:5][CH2:6][O:7][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:16]=1[NH:15][CH:14]=[CH:13]2.[H][H].[CH3:19]I>CN(C=O)C>[CH3:3][O:4][CH2:5][CH2:6][O:7][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:16]=1[N:15]([CH3:19])[CH:14]=[CH:13]2

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 57563295HCID 57563295, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67273994HCID 67273994, compoundYield 85.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a slurry of sodium hydride (60% in mineral oil, 0.575 g, 14 mmol) in DMF (40 mL) was added in portions 7-(2-methoxy-ethoxy)-1H-indole (Cuny, Gregory D.; Yuan, Junying; Jagtap, Prakash; Degterev, Alexei. US 2005119260, 2.5 g, 13 mmol) over 5 minutes at 5-10° C. The reaction mixture was stirred at rt for 1 h until hydrogen evolution ceased, and methyl iodide (3.7 g, 26 mmol) was added dropwise over 5 minutes at 10-20° C. The mixture was stirred at rt for 2 h, quenched with ice/water, and extracted with tert-butylmethyl ether. The organics were washed, dried and concentrated. The residue was crystallized from ether/hexane to yield the desired compound (2.28 g) as a yellowish liquid. MS (ISP): m/e 206.3 (M+H)+

Workup

  1. customquenched with ice/water
  2. extractionextracted with tert-butylmethyl ether
  3. washThe organics were washed
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was crystallized from ether/hexane

Sources & evidence

ORD record
ord-b09bc4388d204319a7ea650c3b68fd62
Source dataset
uspto-grants-2012_04
Patent number
US08163778B2

Reaction notes

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