4-Bromopyridinium chloride → HCID 18007557, compound

HRID 844248Notes

Reaction equation

HRID 844248 reaction equation
[CH3:1][N:2]([CH2:4][CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([Sn](CCCC)(CCCC)CCCC)[CH:13]=2)[CH:8]=[N:7]1)[CH3:3].Cl.Br[C:30]1[CH:35]=[CH:34][N:33]=[CH:32][CH:31]=1>C1(C)C=CC=CC=1>[CH3:3][N:2]([CH2:4][CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:30]3[CH:35]=[CH:34][N:33]=[CH:32][CH:31]=3)[CH:13]=2)[CH:8]=[N:7]1)[CH3:1]

Participants

4

Reactant 2

HCID 881004-Bromopyridinium chlorideHCID 18007542HCID 18007542, compound

Product 1

HCID 18007557HCID 18007557, compoundYield 22.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 1-(2-(N,N-dimethylamino)ethyl)-6-tributylstannyl-1H-indazole (49.1 mg, 0.10 mmol), 4-bromopyridine hydrochloride (21.6 mg, 0.11 mmol), tetrakistriphenylphosphine palladium(0) (10-20 mg, catalytic) in toluene (0.5 mL) was heated at reflux under an inert atmosphere for 18 h. After cooling to room temperature the reaction was quenched by the addition of aqueous sodium hydroxide (1 M, 2 mL) and water (10 mL), and the product extracted into ethyl acetate (50 mL). The organic layer was washed sequentially with water and brine, dried over sodium sulfate and the solvent removed in vacuo. Filtration through an SPE cartridge (Supelco, 6 mL, silica gel, 1000 mg, gradient from 0-10% 2M methanolic ammonia in dichloromethane) gave a crude product which was further purified by flash chromatography (silica gel, 4-10% 2M methanolic ammonia in dichloromethane) to give the title product (6.1 mg, 11%).

Workup

  1. temperatureat reflux under an inert atmosphere for 18 h
  2. customwas quenched by the addition of aqueous sodium hydroxide (1 M, 2 mL) and water (10 mL)
  3. extractionthe product extracted into ethyl acetate (50 mL)
  4. washThe organic layer was washed sequentially with water and brine
  5. dry with materialdried over sodium sulfate
  6. customthe solvent removed in vacuo
  7. filtrationFiltration through an SPE cartridge (Supelco, 6 mL, silica gel, 1000 mg, gradient from 0-10% 2M methanolic ammonia in dichloromethane)
  8. customgave a crude product which
  9. customwas further purified by flash chromatography (silica gel, 4-10% 2M methanolic ammonia in dichloromethane)

Sources & evidence

ORD record
ord-ddd67ff353824d1db570460f45d1ccba
Source dataset
uspto-grants-2002_04
Patent number
US06380242B1

Reaction notes

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