1-(1H-pyrrolo[2,3-c]pyridin-2-yl)ethanol → 1-(1H-pyrrolo[2,3-c]pyridin-2-yl)ethanone

HRID 1821867ノート

反応式

HRID 1821867 の反応式
[NH:1]1[C:5]2=[CH:6][N:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[C:2]1[CH:10]([OH:12])[CH3:11]>C1COCC1.[O-2].[O-2].[Mn+4]>[NH:1]1[C:5]2=[CH:6][N:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[C:2]1[C:10](=[O:12])[CH3:11]

参加物

4

反応物 1

HCID 578934541-(1H-pyrrolo[2,3-c]pyridin-2-yl)ethanol

生成物 1

HCID 552679001-(1H-pyrrolo[2,3-c]pyridin-2-yl)ethanone

試薬・触媒・溶媒 2

HCID 178418406HCID 178418406、化合物触媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 1-(1H-pyrrolo[2,3-c]pyridin-2-yl)ethanol (Example 68) (0.65 g, 4.0 mmol) in THF (80 mL) was added manganese dioxide (4.18 g, 48 mmol). After stirring 2 h at room temperature, TLC analysis indicated that the reaction was completed. The reaction mixture was filtered through diatomaceous earth and rinsed with EtOAc. The filtrate was concentrated and triturated with Et2O to provide 1-(1H-pyrrolo[2,3-c]pyridin-2-yl)ethanone as an off-white solid: mp 236-242° C. dec.; 1H NMR (300 MHz, CD3OD) δ2.63 (3H, s), 7.34 (1H, s), 7.70-7.73 (1H, m), 8.13 (1H, d, J=5.7 Hz), 8.80 (1H, s); ESI MS m/z 161 [C9H8N2O+H]+; HPLC (Method A) 92.7% (AUC), tR=7.75 min.

後処理

  1. filtrationThe reaction mixture was filtered through diatomaceous earth
  2. washrinsed with EtOAc
  3. concentrationThe filtrate was concentrated
  4. customtriturated with Et2O

出典と根拠

ORDレコード
ord-82c0c50ccd6e4d9a894121c27b5cd972
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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