Bromocyclopentane → 2-Chloro-5-cyclopentyloxypyridine

HRID 1260498Notes

Reaction equation

HRID 1260498 reaction equation
[CH:1]1(Br)[CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][N:9]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)=[CH:10][N:9]=1

Participants

5

Reactant 3

HCID 8728Bromocyclopentane2×HCID 10796Cesium carbonate2×HCID 8198212-Chloro-5-hydroxypyridine

Product 1

HCID 583690662-Chloro-5-cyclopentyloxypyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Cyclopentyl bromide (690.3 mg, 4.63 mmol), 2-chloro-5-hydroxypyridine (500 mg, 3.86 mmol) and cesium carbonate (1.51 g, 4.63 mmol) were stirred in 30 ml of DMF at room temperature for 3 h. The reactants had not yet completely reacted. 50% of each of cyclopentyl bromide and cesium carbonate were added, and stirring was continued for 2 h. The reaction mixture was concentrated in vacuo, and the residue was taken up in ethyl acetate and water. The organic phase was separated off and concentrated. Yield: 737 mg (97%), M+H+: 198.08.

Workup

  1. customThe reactants had not yet completely reacted
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customThe organic phase was separated off
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-7178de61e9e6495a9be3bf6bd226a45e
Source dataset
uspto-grants-2013_06
Patent number
US08470841B2

Reaction notes

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