2-methyl-1-(1H-pyrrolo[2,3-c]pyridin-2-yl)-1-propanol → 2-methyl-1-(1H-pyrrolo[2,3-c]pyridin-2-yl)-1-propanone

HRID 1821876ノート

反応式

HRID 1821876 の反応式
[CH3:1][CH:2]([CH3:14])[CH:3]([C:5]1[NH:13][C:8]2=[CH:9][N:10]=[CH:11][CH:12]=[C:7]2[CH:6]=1)[OH:4]>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH3:1][CH:2]([CH3:14])[C:3]([C:5]1[NH:13][C:8]2=[CH:9][N:10]=[CH:11][CH:12]=[C:7]2[CH:6]=1)=[O:4]

参加物

4

反応物 1

HCID 578934892-methyl-1-(1H-pyrrolo[2,3-c]pyridin-2-yl)-1-propanol

生成物 1

HCID 578935262-methyl-1-(1H-pyrrolo[2,3-c]pyridin-2-yl)-1-propanone収率 88%

試薬・触媒・溶媒 2

HCID 178418406HCID 178418406、化合物触媒HCID 6344Dichloromethane溶媒

実験手順

2-Methyl-1-(1H-pyrrolo[2,3-c]pyridin-2-yl)-1-propanol (Example 78) (75 mg, 0.39 mmol) was dissolved in methylene chloride (10 mL). Manganese dioxide (343 mg, 3.94 mmol) was added and the reaction mixture was stirred for ca. 14 h. The reaction mixture was filtered through diatomaceous earth and the filter cake was washed several times with hot methanol. The filtrate was concentrated to give a white solid. Drying under vacuum produced 2-methyl-1-(1H-pyrrolo[2,3-c]pyridin-2-yl)-1-propanone (64 mg, 88%) as a white solid: mp 224-228° C.; 1H NMR (500 MHz, CD3OD) δ1.26 (6H, d, J=7.0 Hz), 3.45-3.62 (1H, m), 7.37 (1H, s), 7.72-7.74 (1H, m), 8.14 (1H, d, J=6.0 Hz), 8.82 (1H, s); ESI MS m/z 189 [C11H12N2O+H]+; HPLC (Method A) 95.4% (AUC), tR=13.7 min.

後処理

  1. filtrationThe reaction mixture was filtered through diatomaceous earth
  2. washthe filter cake was washed several times with hot methanol
  3. concentrationThe filtrate was concentrated
  4. customto give a white solid
  5. customDrying under vacuum

出典と根拠

ORDレコード
ord-fa1de021e23d45ccb0124275c7d3b34b
出典データセット
uspto-grants-2009_10
特許番号
US07608627B2

反応ノート

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