1h-Pyrrolo[2,3-c]pyridine-2-methanol,a-2-pyridinyl- → (pyridin-2-yl)(1H-pyrrolo[2,3-c]pyridin-2-yl)methanone

HRID 1821897ノート

反応式

HRID 1821897 の反応式
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]([C:9]1[NH:17][C:12]2=[CH:13][N:14]=[CH:15][CH:16]=[C:11]2[CH:10]=1)[OH:8]>O1CCCC1.[O-2].[O-2].[Mn+4]>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([C:9]1[NH:17][C:12]2=[CH:13][N:14]=[CH:15][CH:16]=[C:11]2[CH:10]=1)=[O:8]

参加物

4

反応物 1

HCID 578934801h-Pyrrolo[2,3-c]pyridine-2-methanol,a-2-pyridinyl-

生成物 1

HCID 57893522(pyridin-2-yl)(1H-pyrrolo[2,3-c]pyridin-2-yl)methanone収率 112%

試薬・触媒・溶媒 2

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

実験手順

(Pyridin-2-yl)(1H-pyrrolo[2,3-c]pyridin-2-yl)methanol (Example 117) (55 mg, 0.24 mmol) was dissolved in tetrahydrofuran (4 mL). Manganese dioxide (210 mg, 2.42 mmol) was added and the reaction mixture was stirred at room temperature for 2 h. The reaction mixture was filtered through diatomaceous earth and the filter cake was washed thoroughly with tetrahydrofuran. The organic filtrate was concentrated to a yellow solid. Drying under vacuum at 40° C. produced (pyridin-2-yl)(1H-pyrrolo[2,3-c]pyridin-2-yl)methanone (60 mg, quant.): mp 219-222° C.; 1H NMR (500 MHz, CD3OD) δ7.66-7.76 (2H, m), 7.85 (1H, m), 8.04-8.08 (1H, m), 8.14-8.21 (2H, m), 8.82-8.43 (1H, m), 8.92 (1H, s); ESI MS m/z=224 [C13H9N30+H]+; HPLC (Method A) 95.4% (AUC), tR=13.1 min.

後処理

  1. filtrationThe reaction mixture was filtered through diatomaceous earth
  2. washthe filter cake was washed thoroughly with tetrahydrofuran
  3. concentrationThe organic filtrate was concentrated to a yellow solid
  4. customDrying under vacuum at 40° C.

出典と根拠

ORDレコード
ord-fde5535486084025993c3a6bb85d0de6
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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