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Triisopropyl borate → (5-(((tert-Butyldimethylsilyl)oxy)methyl)pyridin-3-yl)boronic acid

HRID 9376
ノート
印刷プレビュー

反応式

HRID 9376 の反応式
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH2:8][O:9][Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11])[CH:7]=1.[B:17](OC(C)C)([O:22]C(C)C)[O:18]C(C)C.C([Li])CCC.[Cl-].[NH4+]>C1COCC1.O>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH2:8][O:9][Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:11])[CH3:12])[CH:7]=1.[Si:10]([O:9][CH2:8][C:6]1[CH:7]=[C:2]([B:17]([OH:22])[OH:18])[CH:3]=[N:4][CH:5]=1)([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 21531Triisopropyl borateHCID 25517Ammonium ChlorideHCID 219840913-Bromo-5-(((tert-butyldimethylsilyl)oxy)methyl)pyridineHCID 178418339Butyllithium

生成物 2

HCID 219840913-Bromo-5-(((tert-butyldimethylsilyl)oxy)methyl)pyridineHCID 21984252(5-(((tert-Butyldimethylsilyl)oxy)methyl)pyridin-3-yl)boronic acid
収率 143.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-20 °C

実験手順

3-Bromo-5-(tert-butyldimethylsilanyloxymethyl)pyridine was prepared according to the published procedure (Zhang, N. et al, J. Med. Chem., 45, 2832–2840 (2002)). Under a nitrogen atmosphere, a solution of 3-bromo-5-(tert-butyldimethylsilanyloxymethyl)pyridine (28.70 g, 94.94 mmol) and triisopropyl borate (26.3 mL, 114 mmol) in dry THF was cooled to −70° C. n-Butyllithium (45.6 mL, 114 mmol) was added dropwise over a period of 1.5 hours. The reaction was stirred for an additional 30 minutes and then allowed to warm to −20° C. Dilute aqueous ammonium chloride was added, and the mixture was allowed to warm to ambient temperature. The aqueous layer was separated and extracted with diethyl ether. The combined organic fractions were concentrated under reduced pressure, and methanol was added to the resulting oil. A solid formed, which was stirred with water for two days, isolated by filtration, and dried under reduced pressure to provide 18.19 g of 5-(tert-butyldimethylsilanyloxymethyl)pyridine-3-boronic acid as a white solid.

後処理

  1. additionwas added dropwise over a period of 1.5 hours
  2. temperatureto warm to ambient temperature
  3. customThe aqueous layer was separated
  4. extractionextracted with diethyl ether
  5. concentrationThe combined organic fractions were concentrated under reduced pressure, and methanol
  6. additionwas added to the resulting oil
  7. customA solid formed
  8. customisolated by filtration
  9. customdried under reduced pressure

出典と根拠

ORDレコード
ord-5d4c45ec99c44e3195ba265c9d851613
出典データセット
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07091214B2

反応ノート

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