2-Bromopyridine → 2-[4-(4-Phenyl-3,6-dihydro-2H-pyridin-1-yl)-but-1-ynyl]-pyridine

HRID 128950Notes

Reaction equation

HRID 128950 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[C:8]1([C:14]2[CH2:15][CH2:16][N:17]([CH2:20][CH2:21][C:22]#[CH:23])[CH2:18][CH:19]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>N1CCCCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:8]1([C:14]2[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][C:22]#[C:23][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=3)[CH2:16][CH:15]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 79732-BromopyridineHCID 11776TriphenylphosphineHCID 107985574-(3,6-Dihydro-4-phenyl-1(2H)-pyridinyl)-1-butyne

Product 1

HCID 105653112-[4-(4-Phenyl-3,6-dihydro-2H-pyridin-1-yl)-but-1-ynyl]-pyridine

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8082PiperidineSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 2-bromopyridine (0.99 mL, 0.01 mol) and the alkyne prepared in Example 9, Step (a) (2.0 g, 0.0095 mol) in 20 mL of piperidine is degassed by bubbling in dry nitrogen for 15 minutes, and 0.03 g (1.4×10-4 mol) of palladium (II) acetate and 0.07 g, (2.8×10-4) of triphenylphosphine are added. The flask is flushed with nitrogen and the mixture is heated at 80° C. for 6 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 extraced 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; mp 87.5°-88.5° C.

Workup

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

Sources & evidence

ORD record
ord-87fff7c2dd1f48b9925ec10306544b1f
Source dataset
uspto-grants-1995_11
Patent number
US05466698

Reaction notes

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