Indole → HCID 17748052, compound

HRID 857308Notes

Reaction equation

HRID 857308 reaction equation
C[Mg+].[Br-].[NH:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5]1.[Cl:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18]Br)=[CH:16][CH:15]=1>CCOCC>[Cl:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18][C:6]2[C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[NH:4][CH:5]=2)=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 798IndoleHCID 693291-(Bromomethyl)-4-chlorobenzeneHCID 178418689HCID 178418689, compound

Product 1

HCID 17748052HCID 17748052, compoundYield 29.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a vigorously stirred solution of 30 mL of 3M MeMgBr in ether was added dropwise a solution of 10 g of indole in 100 mL of ether. After addition was finished, the mixture was heated to reflux for 30 minutes and treated with 22 g of p-chlorobenzyl bromide. The reaction mixture was refluxed for 3 hours, quenched with 50 mL of saturated aqueous solution of NH4Cl, and extracted with 200 mL of ether. The ether layer was dried over Na2SO4 and concentrated. The residue was purified by silica gel flash chromatography eluted with toluene to give 6 g of the title compound as a beige solid.

Workup

  1. additionAfter addition
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 30 minutes
  4. temperatureThe reaction mixture was refluxed for 3 hours
  5. customquenched with 50 mL of saturated aqueous solution of NH4Cl
  6. extractionextracted with 200 mL of ether
  7. dry with materialThe ether layer was dried over Na2SO4
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel flash chromatography
  10. washeluted with toluene

Sources & evidence

ORD record
ord-b720dcfccd2647df8a3b33ae64d25e04
Source dataset
uspto-grants-2006_12
Patent number
US07144913B2

Reaction notes

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