Cesium carbonate → HCID 86625522, compound

HRID 2265950Notes

Reaction equation

HRID 2265950 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[C:9]([O:12][CH2:13][CH2:14]Br)(=[O:11])[CH3:10].C([O-])([O-])=O.[Cs+].[Cs+]>CC#N.CCOC(C)=O>[CH2:13]([O:12][C:9](=[O:11])[CH2:10][O:8][C:5]1[CH:6]=[N:7][C:2]([Cl:1])=[CH:3][CH:4]=1)[CH3:14]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 135641-Acetoxy-2-bromoethaneHCID 8198212-Chloro-5-hydroxypyridine

Product 1

HCID 86625522HCID 86625522, compoundYield 90.1%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 6-chloro-pyridin-3-ol (1000 mg, 7.72 mmol) and bromoethyl acetate (1933 mg, 11.57 mmol) in CH3CN was added Cs2CO3 (3772 mg, 11.57 mmol). The mixture was stirred for overnight at room temperature. The reaction mixture was diluted with EtOAc, then washed three times with H2O and brine, and then dried. MgSO4, filtered and concentrated under reduced pressure. The obtained residue was column-chromatographed to yield the (6-chloro-pyridin-3-yloxy)-acetic acid ethyl ester (1.5 g, 90%).

Workup

  1. washwashed three times with H2O and brine
  2. customdried
  3. filtrationMgSO4, filtered
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was column-chromatographed

Sources & evidence

ORD record
ord-2dee41d38d3349eab8b3549c355e8155
Source dataset
uspto-grants-2010_12
Patent number
US07858621B2

Reaction notes

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