3-Hydroxypyridine → HCID 54121258, compound

HRID 1457919Notes

Reaction equation

HRID 1457919 reaction equation
[CH2:1]([O:5][C:6](=[O:17])[C:7]1[CH:12]=[CH:11][C:10](F)=[C:9]([C:14](=[O:16])[CH3:15])[CH:8]=1)[CH2:2][CH2:3][CH3:4].O[C:19]1[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C)C(=O)N(C)C>[CH2:1]([O:5][C:6](=[O:17])[C:7]1[CH:12]=[CH:11][C:10]([C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)=[C:9]([C:14](=[O:16])[CH3:15])[CH:8]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 79713-HydroxypyridineHCID 10796Cesium carbonateHCID 19047886HCID 19047886, compound

Product 1

HCID 54121258HCID 54121258, compoundYield 69.4%

Reagents, catalysts & solvents 1

HCID 12437TetramethylureaSolvent

Procedure

1.5 g of 3-acetyl-4-fluoro-benzoic acid n-butylester, 0.6 g of 3-hydroxypyridine and 4.1 g of Cs2CO3 are stirred in 20 ml of tetramethylurea for 2 h at 110° C. After cooling to RT the mixture is poured into 200 ml EE and the mixture is washed 3 times with 100 ml brine. Drying takes place over Na2SO4 and the solvent is distilled off in vacuo. Chromatography over silica gel with MTB furnishes 1.3 g of a pale yellow oil. Rf (MTB)=0.30 MS (DCI): 314 (M+H)+

Workup

  1. additionis poured into 200 ml EE
  2. washthe mixture is washed 3 times with 100 ml brine
  3. customDrying
  4. distillationthe solvent is distilled off in vacuo

Sources & evidence

ORD record
ord-b2289f0ddd744960897c88436bca921a
Source dataset
uspto-grants-1998_12
Patent number
US05849775

Reaction notes

Loading…