2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 1H-Pyrrolo[2,3-B]pyridine-5-carboxaldehyde, 1-[(1,1-dimethylethyl)dimethylsilyl]-

HRID 1994195노트

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HRID 1994195 반응식
[C:1]([Si:5]([CH3:18])([CH3:17])[N:6]1[C:10]2=[N:11][CH:12]=[C:13]([CH:15]=[O:16])[CH:14]=[C:9]2[CH2:8][CH2:7]1)([CH3:4])([CH3:3])[CH3:2].C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>C(Cl)Cl.P([O-])([O-])([O-])=O>[C:1]([Si:5]([CH3:18])([CH3:17])[N:6]1[C:10]2=[N:11][CH:12]=[C:13]([CH:15]=[O:16])[CH:14]=[C:9]2[CH:8]=[CH:7]1)([CH3:4])([CH3:3])[CH3:2]

참가 물질

5

반응물 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 587309341-(tert-Butyl-dimethyl-silanyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde

생성물 1

HCID 497590381H-Pyrrolo[2,3-B]pyridine-5-carboxaldehyde, 1-[(1,1-dimethylethyl)dimethylsilyl]-수율 21.1%

시약·촉매·용매 2

HCID 1061Phosphate용매HCID 6344Dichloromethane용매

실험 절차

To a stirred solution of the alcohol 13 (54 mg, 0.20 mmol) in a mixture of CH2Cl2 (15 mL) and 0.2 M pH 7 phosphate buffer (0.15 mL) was added DDQ (53 mg, 0.23 mmol) in three equal portions. When TLC analysis showed complete consumption of the starting material, the mixture was diluted with saturated aqueous NaHCO3 (16 mL) and stirred vigorously for 1 h. The mixture was then extracted with AcOEt (2×). The combined organic solutions were washed with saturated brine (1×), dried (MgSO4) and concentrated. The residue was purified by PTLC with benzene as eluent to afford aldehyde 16 (11 mg, 21%). 1H NMR (400 MHz; CDCl3) δ 0.66 (s, 6H), 0.94 (s, 9H), 6.67 (d, J=3.5 Hz, 1H), 7.34 (d, J=3.5 Hz, 1H), 8.37 (d, J=2.0 Hz, 1H), 8.76 (d, J=2.0 Hz, 1H), 10.11 (s, 1H).

후처리

  1. customconsumption of the starting material
  2. additionthe mixture was diluted with saturated aqueous NaHCO3 (16 mL)
  3. extractionThe mixture was then extracted with AcOEt (2×)
  4. washThe combined organic solutions were washed with saturated brine (1×)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customThe residue was purified by PTLC with benzene as eluent

출처 및 근거

ORD 기록
ord-7c47729854e84166a95217da17562829
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07652137B2

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