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

HRID 599457

反応式

HRID 599457 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

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-2e60ae61b83048c6b9a61865faebcc5b
出典データセット
uspto-grants-2011_03
特許番号
US07897767B2

関連ノート

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