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

HRID 347529ノート

反応式

HRID 347529 の反応式
[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

参加物

8

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-40 °C

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-81d53db54a5c48bf9789e8a913efefab
出典データセット
uspto-grants-2007_02
特許番号
US07173031B2

反応ノート

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