Hydrochloric Acid → (4-chloro-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridin-2-yl)boronic acid

HRID 347529노트

반응식

HRID 347529 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[CH:9]=[CH:10][C:3]=12.[Li]CCCC.C([O:27][B:28](OC(C)C)[O:29]C(C)C)(C)C.Cl.OP([O-])([O-])=O.[K+].[K+]>C1COCC1.O>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[C:9]([B:28]([OH:29])[OH:27])=[CH:10][C:3]=12

참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 21531Triisopropyl borateHCID 24450Potassium Phosphate, DibasicHCID 116735894-Chloro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo(2,3-b)pyridineHCID 178418339Butyllithium

생성물 1

HCID 21081673(4-chloro-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridin-2-yl)boronic acid

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
-40 °C

실험 절차

To a solution of 4-chloro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridine (565 mg, 2 mmol) in THF (5 mL) at −40° C. under N2, was added n-BuLi (2.0 M in cyclohexane, Aldrich, 2.4 mmol). The reaction mixture was stirred at −40° C. for 1 h and then treated with triisopropylborate (489 mg, 2.6 mmol). The mixture was slowly warmed to rt and stirred overnight. To this solution was added 1 N HCl in H2O (20 mL), and the mixture was stirred for 20 min., neutralized with saturated aq. K2HPO4 solution and extracted with ether. The organic layer was dried over Na2SO4. After filtration and concentration under reduced pressure, the title compound was obtained as a light beige solid (640 mg, quantitative yield). LC/MS(ESI+) m/z 327 (M+H)+.

후처리

  1. temperatureThe mixture was slowly warmed to rt
  2. stirringstirred overnight
  3. stirringthe mixture was stirred for 20 min.
  4. extractionextracted with ether
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationAfter filtration and concentration under reduced pressure

출처 및 근거

ORD 기록
ord-81d53db54a5c48bf9789e8a913efefab
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07173031B2

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