2-Pyridinecarboxamide → HCID 58119352, compound

HRID 2167492Notes

Reaction equation

HRID 2167492 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:7][CH:6]=1)=O.[N:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:21]([NH2:23])=[O:22]>>[CH3:14][S:11]([C:8]1[CH:9]=[CH:10][C:5]([C:3]2[N:23]=[C:21]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][N:15]=3)[O:22][CH:2]=2)=[CH:6][CH:7]=1)(=[O:13])=[O:12]

Participants

3

Reactant 2

HCID 150702-PyridinecarboxamideHCID 7358232-Bromo-4'-(methylsulfonyl)acetophenone

Product 1

HCID 58119352HCID 58119352, compoundYield 3.9%

Conditions

Temperature
150 °C

Procedure

The mixture of the 2-bromo-1-[4-(methylsulfonyl)phenyl]ethanone (500 mg, 1.8 mmol) and pyridine 2-carboxamide (551 mg, 4.51 mmol) was heated to 150° C. for 1 hour. Then the reaction mixture was cooled, and partitioned between ethyl acetate and water. The aqueous layer was extracted with ethyl acetate twice, and the combined organic layers were washed with water and brine, dried over MgSO4. After concentration, the solid residue was dissolved in methanol and subject to mass-directed HPLC purification to give 21 mg of 2-{4-[4-(methylsulfonyl)phenyl]-1,3-oxazol-2-yl}pyridine. LCMS: m/z 301.0 (M+H)+.

Workup

  1. temperatureThen the reaction mixture was cooled
  2. custompartitioned between ethyl acetate and water
  3. extractionThe aqueous layer was extracted with ethyl acetate twice
  4. washthe combined organic layers were washed with water and brine
  5. dry with materialdried over MgSO4
  6. concentrationAfter concentration
  7. dissolutionthe solid residue was dissolved in methanol
  8. customsubject to mass-directed HPLC purification

Sources & evidence

ORD record
ord-55dba9d953ee4435934bd832e8ce47e8
Source dataset
uspto-grants-2015_06
Patent number
US09045467B2

Reaction notes

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