Water → 2-(Methylsulfonyl)thiazolo[5,4-b]pyridine

HRID 707275

反応式

HRID 707275 の反応式
[CH3:1][S:2][C:3]1[S:4][C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][N:6]=2.[Mn]([O-])(=O)(=O)=[O:13].[K+].[OH2:18]>C(O)(=O)C>[CH3:1][S:2]([C:3]1[S:4][C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][N:6]=2)(=[O:13])=[O:18]

参加物

5

反応物 3

HCID 962WaterHCID 516875Potassium Permanganate2 回HCID 6998402-(Methylthio)thiazolo[5,4-b]pyridine

生成物 1

HCID 36045032-(Methylsulfonyl)thiazolo[5,4-b]pyridine収率 20.1%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

To a stirred, room temperature solution of 2-(methylthio)thiazolo[5,4-b]pyridine (182 mg, 1.0 mmol) in acetic acid (10 mL) was added a solution of potassium permanganate (47.3 mg, 0.3 mmol) in water (6 mL) dropwise. The reaction mixture was stirred at room temperature for 16 h. LCMS showed incomplete conversion. Additional KMnO4 (158 mg) was mixed in and stirred for another 5 h. LCMS showed complete conversion. The reaction mixture was quenched with aqueous sodium sulfite. The resulting mixture was vigorously stirred at room temperature overnight. The resulting solution was partitioned between EtOAc and saturated Na2CO3. The aqueous layer was extracted with ethyl acetate, dried (Na2SO4), and concentrated. To the residue was added aq. Na2CO3 until the pH reaches 7. The precipitate formed was collected by filtration, dried to give 2-(methylsulfonyl)thiazolo[5,4-b]pyridine (43 mg, 0.201 mmol, 20.10% yield) as a tan solid. 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 3.42 (s, 3 H) 7.62 (dd, J=8.40, 4.60 Hz, 1 H) 8.47 (dd, J=8.33, 1.46 Hz, 1 H) 8.75-8.84 (m, 1H). EST (M+1) 214.9.

後処理

  1. stirringstirred for another 5 h
  2. customThe reaction mixture was quenched with aqueous sodium sulfite
  3. stirringThe resulting mixture was vigorously stirred at room temperature overnight
  4. customThe resulting solution was partitioned between EtOAc and saturated Na2CO3
  5. extractionThe aqueous layer was extracted with ethyl acetate
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. additionTo the residue was added aq. Na2CO3 until the pH
  9. customThe precipitate formed
  10. filtrationwas collected by filtration
  11. customdried

出典と根拠

ORDレコード
ord-52fceaeb7d9140889103e9e33fbf4d89
出典データセット
uspto-grants-2015_11
特許番号
US09174992B2

関連ノート

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