Sodium hydride → 5-Bromo-2-(2-(pyrrolidin-1-yl)ethoxy)pyridine

HRID 1916567Notes

Reaction equation

HRID 1916567 reaction equation
[H-].[Na+].[OH:3][CH2:4][CH2:5][N:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1.Br[C:12]1[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][N:13]=1>CN(C=O)C.CCOC(C)=O>[Br:18][C:15]1[CH:16]=[CH:17][C:12]([O:3][CH2:4][CH2:5][N:6]2[CH2:10][CH2:9][CH2:8][CH2:7]2)=[N:13][CH:14]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 693532,5-DibromopyridineHCID 762881-Pyrrolidineethanol

Product 1

HCID 105881665-Bromo-2-(2-(pyrrolidin-1-yl)ethoxy)pyridine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

280 mg (7.00 mmol, 60%) NaH are added to a solution of 0.76 mL (6.14 mmol) N-(2-hydroxyethyl)pyrrolidine in 20 mL DMF at RT. The reaction solution is stirred for 45 min at RT and then 1.35 g (5.53 mmol) 2,5-dibromopyridine are added. The solution is stirred for 16 h at 70° C. and the solvent is eliminated i.vac. The residue is taken up in 100 mL EtOAc and 50 mL water and the organic phase is extracted with 40 mL saturated NaCl solution. The organic phase is dried over Na2SO4 and the solvent is eliminated i.vac. Further purification is carried out by column chromatography on silica gel (gradient: cyc/EtOAc 1:1 to EtOAc).

Workup

  1. stirringThe solution is stirred for 16 h at 70° C.
  2. extraction50 mL water and the organic phase is extracted with 40 mL saturated NaCl solution
  3. dry with materialThe organic phase is dried over Na2SO4
  4. customFurther purification

Sources & evidence

ORD record
ord-7d21ed10f3b243e2baf28da65ca4bfbf
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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