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

HRID 1994188노트

반응식

HRID 1994188 반응식
[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]

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 516892Sodium Bicarbonate용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-89e7897693094c5c86e2c7fa7ce0bb28
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07652137B2

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