Tetrahydrofuran → 1-(3-Methyl-3H-benzotriazol-5-yl)-2-(6-methyl-pyridin-2-yl)-ethanone

HRID 1868335Notes

Reaction equation

HRID 1868335 reaction equation
CON(C)[C:4]([C:6]1[CH:15]=[CH:14][C:9]2[N:10]=[N:11][N:12]([CH3:13])[C:8]=2[CH:7]=1)=[O:5].O1[CH2:21][CH2:20][CH2:19][CH2:18]1>>[CH3:13][N:12]1[C:8]2[CH:7]=[C:6]([C:4](=[O:5])[CH2:18][C:19]3[CH:20]=[CH:21][CH:8]=[C:9]([CH3:14])[N:10]=3)[CH:15]=[CH:14][C:9]=2[N:10]=[N:11]1

Participants

3

Reactant 2

HCID 8028TetrahydrofuranHCID 859571723-methyl-3H-benzotriazole-5-carboxylic acid methoxy-methyl-amide

Product 1

HCID 688986501-(3-Methyl-3H-benzotriazol-5-yl)-2-(6-methyl-pyridin-2-yl)-ethanoneYield 53%

Procedure

−30° C. for 1 hour. In a separate flask, a solution of 3-methyl-3H-benzotriazole-5-carboxylic acid methoxy-methyl-amide (500 mg, 2.27 mmol) in 3 ml anhydrous tetrahydrofuran was cooled to −30° C. The cold anion solution was slowly added dropwise to the cold amide solution. Once the addition was complete, the reaction was allowed to slowly warm to room temperature over several hours and stirred overnight. The reaction was quenched with water and the solvent removed by rotary evaporation. The residue was dissolved in saturated aqueous ammonium chloride and extracted three times with chloroform. The combined organics were washed once with water and then once with brine. The combined organics were dried over sodium sulfate, filtered and concentrated to dryness. Crude material was purified on Biotage Flash 40S silica gel column using hexanes/ethyl acetate gradient system (80:20 to 40:60, respectively) as eluent to afford 1-(3-Methyl-3H-benzotriazol-5-yl)-2-(6-methyl-pyridin-2-yl)-ethanone (320 mg, 53%).

Workup

  1. additionOnce the addition
  2. customThe reaction was quenched with water
  3. customthe solvent removed by rotary evaporation
  4. dissolutionThe residue was dissolved in saturated aqueous ammonium chloride
  5. extractionextracted three times with chloroform
  6. washThe combined organics were washed once with water
  7. dry with materialThe combined organics were dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated to dryness
  10. customCrude material was purified on Biotage Flash 40S silica gel column

Sources & evidence

ORD record
ord-9db78959e3dd4c9ca89a30ec535b5206
Source dataset
uspto-grants-2009_12
Patent number
US07635702B2

Reaction notes

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