Hydrogen Peroxide → 5-Chloro-6-((3,3-difluorocyclobutyl)methoxy)pyridin-3-OL

HRID 512061ノート

反応式

HRID 512061 の反応式
[Cl:1][C:2]1[C:3]([O:17][CH2:18][CH:19]2[CH2:22][C:21]([F:24])([F:23])[CH2:20]2)=[N:4][CH:5]=[C:6](B2OC(C)(C)C(C)(C)O2)[CH:7]=1.OO.S([O-])([O-:29])=S>CO>[Cl:1][C:2]1[CH:7]=[C:6]([OH:29])[CH:5]=[N:4][C:3]=1[O:17][CH2:18][CH:19]1[CH2:22][C:21]([F:24])([F:23])[CH2:20]1

参加物

5

反応物 3

HCID 784Hydrogen PeroxideHCID 9548651Thiosulfite(2-)HCID 580424833-Chloro-2-((3,3-difluorocyclobutyl)methoxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)pyridine

生成物 1

HCID 580423895-Chloro-6-((3,3-difluorocyclobutyl)methoxy)pyridin-3-OL収率 81%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

3-Chloro-2-[(3,3-difluorocyclobutyl)methoxy]-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (Preparation 38, 4.5 g, 12.5 mmol) was suspended in methanol (30 mL). Hydrogen peroxide (1.6 mL, 21.3 mmol) was added and the mixture stirred at room temperature under nitrogen for 16 hours. An aqueous solution of thiosulfite (10%, 10 mL) was added and the mixture was extracted with EtOAc (2×200 mL). The combined organics were dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (Biotage®, gradient of 0-50% EtOAc in heptane) to afford the title compound (2.53 g, 81%).

後処理

  1. extractionthe mixture was extracted with EtOAc (2×200 mL)
  2. dry with materialThe combined organics were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel chromatography (Biotage®, gradient of 0-50% EtOAc in heptane)

出典と根拠

ORDレコード
ord-760529be6cd646738e14bb8ab900c714
出典データセット
uspto-grants-2015_08
特許番号
US09102621B2

反応ノート

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