Water → HCID 58220156, compound

HRID 40717Notes

Reaction equation

HRID 40717 reaction equation
Cl[C:2]1[C:7]([NH:8][C:9](=[O:18])[C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)=[CH:6][CH:5]=[C:4]([Cl:19])[N:3]=1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[Cl:19][C:4]1[N:3]=[C:2]2[O:18][C:9]([C:10]3[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=3)=[N:8][C:7]2=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 58220150N-(2,6-dichloro-pyridin-3-yl)-4-methoxy-benzamide

Product 1

HCID 58220156HCID 58220156, compoundYield 59.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
160 °C

Procedure

N-(2,6-Dichloro-pyridin-3-yl)-4-methoxy-benzamide (3.86 g, 13.0 mmol) and K2CO3 (1.80 g, 13 mmol) were combined in DMF (15 mL) and heated by microwave to 160° C. for 30 minutes. The resulting mixture was poured into water (100 mL) causing the formation of a precipitate which was collected by filtration and washed with additional water before drying overnight in vacuo. The resulting solid was purified with silica gel flash chromatography (0-60% EtOAc in hexanes) to afford 5-chloro-2-(4-methoxy-phenyl)-oxazolo[5,4-b]pyridine (2.0 g, 7.67 mmol, 59.1% yield) which was used in subsequent reactions without further purification. ES MS (M+H+)=261.

Workup

  1. filtrationwas collected by filtration
  2. washwashed with additional water
  3. custombefore drying overnight in vacuo
  4. customThe resulting solid was purified with silica gel flash chromatography (0-60% EtOAc in hexanes)

Sources & evidence

ORD record
ord-066f0a9fb8014c528d829895a2a6db74
Source dataset
uspto-grants-2013_09
Patent number
US08530483B2

Reaction notes

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