2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 1-(tert-Butyl-dimethyl-silanyl)-5-methyl-1H-pyrrolo[2,3-b]pyridine

HRID 1994188ノート

反応式

HRID 1994188 の反応式
[C:1]([Si:5]([CH3:17])([CH3:16])[N:6]1[C:10]2=[N:11][CH:12]=[C:13]([CH3:15])[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.C([O-])(O)=O.[Na+]>[C:1]([Si:5]([CH3:17])([CH3:16])[N:6]1[C:10]2=[N:11][CH:12]=[C:13]([CH3:15])[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 575977571-(tert-Butyl-dimethyl-silanyl)-5-methyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine

生成物 1

HCID 575978501-(tert-Butyl-dimethyl-silanyl)-5-methyl-1H-pyrrolo[2,3-b]pyridine

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

To a stirred solution of the crude azaindoline 7 (0.64 mmol) in CH2Cl2 (10 mL) was added DDQ (145 mg, 0.64 mmol) in one portion. After 20 min the resulting black mixture was diluted with saturated aqueous NaHCO3 solution and stirred vigorously for 15 min. The aqueous layer was extracted with CHCl3 (2×) and the combined organic solutions were dried (MgSO4), filtered and concentrated to afford azaindole 8 as a brown oil, which was used directly in the next step without purification.

後処理

  1. extractionThe aqueous layer was extracted with CHCl3 (2×)
  2. dry with materialthe combined organic solutions were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-89e7897693094c5c86e2c7fa7ce0bb28
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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