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 1821876노트

반응식

HRID 1821876 반응식
[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]

참가 물질

4

반응물 1

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

생성물 1

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

시약·촉매·용매 2

HCID 178418406HCID 178418406, 화합물촉매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-fa1de021e23d45ccb0124275c7d3b34b
출처 데이터셋
uspto-grants-2009_10
특허 번호
US07608627B2

반응 노트

불러오는 중…