5-Bromoindole → 5-[4-(3,6-Dihydro-4-phenyl-1(2H)-pyridinyl)-1-butynyl]-1H-indole

HRID 128951Notes

Reaction equation

HRID 128951 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.[C:11]1([C:17]2[CH2:18][CH2:19][N:20]([CH2:23][CH2:24][C:25]#[CH:26])[CH2:21][CH:22]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(N)CCC>[C:11]1([C:17]2[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][C:25]#[C:26][C:2]3[CH:3]=[C:4]4[C:8](=[CH:9][CH:10]=3)[NH:7][CH:6]=[CH:5]4)[CH2:19][CH:18]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 249055-BromoindoleHCID 107985574-(3,6-Dihydro-4-phenyl-1(2H)-pyridinyl)-1-butyne

Product 1

HCID 107112545-[4-(3,6-Dihydro-4-phenyl-1(2H)-pyridinyl)-1-butynyl]-1H-indole

Reagents, catalysts & solvents 1

HCID 8007ButylamineSolvent

Procedure

A solution of 5-bromoindole (0.5 g, 0.0025 mol) and the acetylene prepared in Example 9, Step (a) in 15 mL of N-butylamine is degassed by bubbling in dry nitrogen for 15 minutes, and 0.06 g, (5.0×10-5 mol) of tetrakis (triphenylphosphine)palladium(O) is added. The flask is flushed with nitrogen and the mixture is headed at reflux for 18 hours. The solvent is removed under reduced pressure, and the residue is partitioned between 50 mL of dichloromethane and 50 mL of saturated aqueous sodium bicarbonate. The aqueous layer is extracted with 25 mL of dichloromethane and the combined organic layers are washed with 25 mL of water and dried (sodium sulfate), and the solvent is removed in vacuo. The residue is chromatographed (silica gel, 1% methanol/99% dichloromethane) to give the title compound containing 0.3 mol of water; mp 173°-174° C.

Workup

  1. customby bubbling in dry nitrogen for 15 minutes
  2. customThe flask is flushed with nitrogen
  3. temperatureat reflux for 18 hours
  4. customThe solvent is removed under reduced pressure
  5. customthe residue is partitioned between 50 mL of dichloromethane and 50 mL of saturated aqueous sodium bicarbonate
  6. extractionThe aqueous layer is extracted with 25 mL of dichloromethane
  7. washthe combined organic layers are washed with 25 mL of water
  8. dry with materialdried (sodium sulfate)
  9. customthe solvent is removed in vacuo
  10. customThe residue is chromatographed (silica gel, 1% methanol/99% dichloromethane)

Sources & evidence

ORD record
ord-22666eeda72b40c5a60f275a04f54a9e
Source dataset
uspto-grants-1995_11
Patent number
US05466698

Reaction notes

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