1-Bromooctane → HCID 49782540, compound

HRID 1484422Notes

Reaction equation

HRID 1484422 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[CH:7]2.Br[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]>CN(C)C=O>[Br:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH:8]=[CH:7]2

Participants

5

Reactant 3

HCID 81401-BromooctaneHCID 24758Sodium hydrideHCID 249055-Bromoindole

Product 1

HCID 49782540HCID 49782540, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a stirred suspension of sodium hydride (NaH, 60% dispersion in mineral oil; 48 mg, 2 mmol) in anhydrous dimethylformamide (5 ml) in an ice bath was added dropwise a solution of 5-bromo 1H indole (1.5 mmol) in anhydrous DMF (10 mL) over a period of 10 min at 0 C. After stirring for 10 min, 1-Bromooctane (1.8 mmol) was added drop wise over 5 min and reaction mixture was allowed to warm to RT and left with stirring for overnight. The reaction was quenched by pouring over ice and extracted twice with ethyl acetate (25 ml). The combined organic layers were washed with brine, dried (Na2SO4), filtered and concentrated under reduced pressure to obtain the crude residue. The crude material was purified by flash silica gel column chromatography with ethyl acetate and Hexane to get 5-bromo 1-octyl 1H-indole as an oil (Yield: 80 to 90%). Product was confirmed by NMR and LC-MS

Workup

  1. customreaction mixture
  2. waitleft
  3. stirringwith stirring for overnight
  4. customThe reaction was quenched
  5. additionby pouring over ice
  6. extractionextracted twice with ethyl acetate (25 ml)
  7. washThe combined organic layers were washed with brine
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customto obtain the crude residue
  12. customThe crude material was purified by flash silica gel column chromatography with ethyl acetate and Hexane

Sources & evidence

ORD record
ord-d5bb1cbbeb3947ee9b60f15a294ee97d
Source dataset
uspto-grants-2016_08
Patent number
US09422238B2

Reaction notes

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