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

HRID 1821897노트

반응식

HRID 1821897 반응식
[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]

참가 물질

4

반응물 1

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

생성물 1

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

시약·촉매·용매 2

HCID 178418406HCID 178418406, 화합물촉매HCID 8028Tetrahydrofuran용매

실험 절차

(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.

후처리

  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.

출처 및 근거

ORD 기록
ord-fde5535486084025993c3a6bb85d0de6
출처 데이터셋
uspto-grants-2009_10
특허 번호
US07608627B2

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