Allyl bromide → HCID 59409488, compound

HRID 659950Notes

Reaction equation

HRID 659950 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[C:8]([C:10]2[NH:18][C:17]3[C:12](=[N:13][CH:14]=[CH:15][CH:16]=3)[C:11]=2[C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)[CH:7]=[CH:6][N:5]=1.[CH2:26](Br)[CH:27]=[CH2:28].[Cl-].[NH4+]>CN(C)C=O>[CH2:28]([N:18]1[C:17]2[C:12](=[N:13][CH:14]=[CH:15][CH:16]=2)[C:11]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)=[C:10]1[C:8]1[CH:7]=[CH:6][N:5]=[C:4]([Cl:3])[CH:9]=1)[CH:27]=[CH2:26]

Participants

6

Reactant 4

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 10871025HCID 10871025, compound

Product 1

HCID 59409488HCID 59409488, compoundYield 74.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (120 mg, 3 mmole 60% in oil) is added to a solution of 323.5 mg (1 mmole) of 2-(2-Chloro-pyridin-4-yl)-3-(4-fluoro-phenyl)-1H-pyrrolo[3,2-b]pyridine in 8 mL of dimethylformamide at room temperature. After 30 min. at room temperature, 1.2 g of allyl bromide (10 mmoles) is added to the reaction mixture. After 1 hour at room temperature, the reaction mixture is poured into ammonium chloride solution and extracted with ethyl acetate. The organic phase is washed with water and dried over magnesium sulfate. After concentration the solid residue is purified by chromatography on silica gel (ethyl acetate/hexane 1/1) to give 270 mg of 1-Allyl-2-(2-chloro-pyridin-4-yl)-3-(4-fluoro-phenyl)-1H-pyrrolo[3,2-b]pyridine as white solid.

Workup

  1. waitAfter 1 hour at room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic phase is washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationAfter concentration the solid residue
  6. customis purified by chromatography on silica gel (ethyl acetate/hexane 1/1)

Sources & evidence

ORD record
ord-78b44139cf1644918704d55116bcb33f
Source dataset
uspto-grants-2011_12
Patent number
US08084395B2

Reaction notes

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