Iodoethane → 6-bromo-1-ethyl-4-methoxy-1H-indole

HRID 1404143Notes

Reaction equation

HRID 1404143 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[CH:9][NH:10]2)=[C:6]([O:13][CH3:14])[CH:5]=1.[CH2:15](I)[CH3:16]>CN(C=O)C>[Br:3][C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[CH:9][N:10]2[CH2:15][CH3:16])=[C:6]([O:13][CH3:14])[CH:5]=1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 247280346-Bromo-4-methoxy-1H-indole

Product 1

HCID 583039096-bromo-1-ethyl-4-methoxy-1H-indoleYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

NaH (96 mg, 4 mmol) was suspended in 7 mL DMF in a round bottom flask and cooled to 0° C. 6-bromo-4-methoxy-1H-indole (0.75 g, 3.3 mmol) was added dropwise as a solution in DMF (1 mL). Ethyl iodide (0.28 mL, 3.5 mmol) was added dropwise and the reaction mixture was stirred for 10 min. Volatiles were removed under reduced pressure and the residue partitioned between DCM and water. The aqueous layer was extracted with DCM and the combined organics layers were dried over MgSO4, filtered, and evaporated to give a red oil. The resulting residue was purified on silica gel column chromatography eluting with hexanes/ethyl acetate (0-10%) to afford pure 36-2 (584 mg, 70%) as a white solid.

Workup

  1. customVolatiles were removed under reduced pressure
  2. customthe residue partitioned between DCM and water
  3. extractionThe aqueous layer was extracted with DCM
  4. dry with materialthe combined organics layers were dried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customto give a red oil
  8. customThe resulting residue was purified on silica gel column chromatography
  9. washeluting with hexanes/ethyl acetate (0-10%)

Sources & evidence

ORD record
ord-46ae00ab12b14aad83e3e3d37620f1fb
Source dataset
uspto-grants-2014_12
Patent number
US08912220B2

Reaction notes

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