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

HRID 1994195ノート

反応式

HRID 1994195 の反応式
[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]

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 1061Phosphate溶媒HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-7c47729854e84166a95217da17562829
出典データセット
uspto-grants-2010_01
特許番号
US07652137B2

反応ノート

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