Imidazole → 3-((5-Bromo-2-methoxyphenyl)(tert-butyldimethylsilyloxy)methyl)-2,6-difluoropyridine

HRID 335902ノート

反応式

HRID 335902 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:18][CH3:19])=[C:6]([CH:8]([C:10]2[C:11]([F:17])=[N:12][C:13]([F:16])=[CH:14][CH:15]=2)[OH:9])[CH:7]=1.N1C=CN=C1.[C:25]([Si:29](Cl)([CH3:31])[CH3:30])([CH3:28])([CH3:27])[CH3:26].O>CN(C=O)C.C(OCC)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:18][CH3:19])=[C:6]([CH:8]([O:9][Si:29]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:31])[CH3:30])[C:10]2[C:11]([F:17])=[N:12][C:13]([F:16])=[CH:14][CH:15]=2)[CH:7]=1

参加物

7

反応物 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 67383458(5-Bromo-2-methoxyphenyl)(2,6-difluoropyridin-3-yl)methanol

生成物 1

HCID 673831653-((5-Bromo-2-methoxyphenyl)(tert-butyldimethylsilyloxy)methyl)-2,6-difluoropyridine

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
70 °C

実験手順

(5-Bromo-2-methoxyphenyl)(2,6-difluoropyridin-3-yl)methanol (13.77 g, 41.7 mmol) and imidazole (3.41 g, 50.1 mmol) were dissolved in dry DMF (20 mL) under nitrogen. t-Butyl(chloro)dimethylsilane (6.92 g, 45.9 mmol) was added and the solution heated to 70° C. After 1 hour the mixture was cooled to RT. Water (200 mL) and diethyl ether (200 mL) were added and the phases mixed and separated. The organic was washed with water (200 mL) one more time then dried with magnesium sulfate and evaporated to dryness under reduced pressure. Purification using silica chromatography (hexane to 1:1 DCM: hexane gradient) gave 3-((5-bromo-2-methoxyphenyl)(tert-butyldimethylsilyloxy)methyl)-2,6-difluoropyridine as a thick oil that solidified on standing.

後処理

  1. temperatureAfter 1 hour the mixture was cooled to RT
  2. additionthe phases mixed
  3. customseparated
  4. washThe organic was washed with water (200 mL) one more time
  5. dry with materialthen dried with magnesium sulfate
  6. customevaporated to dryness under reduced pressure
  7. customPurification

出典と根拠

ORDレコード
ord-177acd573d094f4ead0f1d968a405d05
出典データセット
uspto-grants-2014_11
特許番号
US08883782B2

反応ノート

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