2-Fluoroethyl bromide → HCID 86643499, compound

HRID 659953Notes

Reaction equation

HRID 659953 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.Br[CH2:27][CH2:28][F:29].[Cl-].[NH4+]>CN(C)C=O>[Cl:3][C:4]1[CH:9]=[C:8]([C:10]2[N:18]([CH2:27][CH2:28][F:29])[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

Participants

6

Reactant 4

HCID 129822-Fluoroethyl bromideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 10871025HCID 10871025, compound

Product 1

HCID 86643499HCID 86643499, compoundYield 62.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (371 mg, 9.3 mmoles 60% in oil) is added to a solution of 1 g (3.1 mmoles) of 2-(2-Chloro-pyridin-4-yl)-3-(4-fluoro-phenyl)-1H-pyrrolo[3,2-b]pyridine (prepared following the procedure for example 6) in 20 mL of dimethylformamide at room temperature. After 30 min. at room temperature, 2.75 g of 1-bromo-2-fluoro-ethane (21.6 mmoles) is added to the reaction mixture. After 10 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 720 mg of 2-(2-Chloro-pyridin-4-yl)-1-(2-fluoro-ethyl)-3-(4-fluoro-phenyl)-1H-pyrrolo[3,2-b]pyridine as white solid.

Workup

  1. customprepared
  2. customat room temperature
  3. waitAfter 10 hour at room temperature
  4. extractionextracted with ethyl acetate
  5. washThe organic phase is washed with water
  6. dry with materialdried over magnesium sulfate
  7. concentrationAfter concentration the solid residue
  8. customis purified by chromatography on silica gel (ethyl acetate/hexane 1/1)

Sources & evidence

ORD record
ord-a2249097ab654673a35db6e03cb522c7
Source dataset
uspto-grants-2011_12
Patent number
US08084395B2

Reaction notes

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