1h-Pyrrolo[2,3-c]pyridine-2-methanol,a-(4-methylphenyl)- → (4-methylphenyl)(1H-pyrrolo[2,3-c]pyridin-2-yl)methanone

HRID 1821885노트

반응식

HRID 1821885 반응식
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:10]2[NH:18][C:13]3=[CH:14][N:15]=[CH:16][CH:17]=[C:12]3[CH:11]=2)[OH:9])=[CH:4][CH:3]=1>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:10]2[NH:18][C:13]3=[CH:14][N:15]=[CH:16][CH:17]=[C:12]3[CH:11]=2)=[O:9])=[CH:6][CH:7]=1

참가 물질

4

반응물 1

HCID 578934571h-Pyrrolo[2,3-c]pyridine-2-methanol,a-(4-methylphenyl)-

생성물 1

HCID 57893512(4-methylphenyl)(1H-pyrrolo[2,3-c]pyridin-2-yl)methanone수율 67.1%

시약·촉매·용매 2

HCID 178418406HCID 178418406, 화합물촉매HCID 6344Dichloromethane용매

실험 절차

(4-Methylphenyl)(1H-pyrrolo[2,3-c]pyridin-2-yl)methanol (Example 98) (225 mg, 0.94 mmol) was dissolved in methylene chloride (15 mL). Manganese dioxide (817 mg, 9.40 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 ethanol. The filtrate was concentrated to give a white solid. Drying under vacuum produced (4-methylphenyl)(1H-pyrrolo[2,3-c]pyridin-2-yl)methanone (149 mg, 67%) as a white solid: mp 264-268° C. dec.; 1H NMR (300 MHz, CD3OD) δ2.47 (3H, s), 7.18 (1H, s), 7.41 (2H, d, J=7.9 Hz), 7.73-7.75 (1H, m), 7.92 (2H, d, J=8.1 Hz), 8.16 (1H, d, J=5.6 Hz), 8.87 (1H, s); ESI MS m/z 237 [C15H12N2O+H]+; HPLC (Method A) 93.4% (AUC), tR=15.9 min.

후처리

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

출처 및 근거

ORD 기록
ord-b4a0acdea8374ba086525c42a273fefb
출처 데이터셋
uspto-grants-2009_10
특허 번호
US07608627B2

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