3-Hydroxypyridine → HCID 57870511, compound

HRID 1661200Notes

Reaction equation

HRID 1661200 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N:8]2[CH:12]=[C:11]([C:13](=[O:16])[CH2:14]Cl)[N:10]=[CH:9]2)[CH:5]=[CH:6][CH:7]=1.[OH:17][C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([N:8]2[CH:12]=[C:11]([C:13](=[O:16])[CH2:14][O:17][C:18]3[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=3)[N:10]=[CH:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 79713-HydroxypyridineHCID 11430Potassium CarbonateHCID 86634423HCID 86634423, compound

Product 1

HCID 57870511HCID 57870511, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1-[1-(3-Bromo-phenyl)-1H-imidazol-4-yl]-2-chloro-ethanone 4 (60 mg; 0.17 mmol) was dissolved in acetone (5 mL). 3-Hydroxypyridine (22 mg; 0.23 mmol) and K2CO3 (117 mg; 0.85 mmol) were added and heated to reflux for 16 h. The mixture was partitioned between EtOAc and water. The organic phase was then washed with 2N NaOH, saturated aqueous NaCl and was dried over Na2SO4. Concentration of the organic layer afforded 15 mg (25%) of 5. HRMS (ESI+): m/z=358.1938 [M+H]

Workup

  1. temperatureheated
  2. temperatureto reflux for 16 h
  3. customThe mixture was partitioned between EtOAc and water
  4. washThe organic phase was then washed with 2N NaOH, saturated aqueous NaCl
  5. dry with materialwas dried over Na2SO4

Sources & evidence

ORD record
ord-6e18c730696b4a9889b1193952e8222f
Source dataset
uspto-grants-2011_10
Patent number
US08030339B2

Reaction notes

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