Water → GS-458967

HRID 406415

反応式

HRID 406415 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]([F:14])([F:13])[F:12])=[N:9][N:10]=2)[CH:7]=1.[F:15][C:16]([F:28])([F:27])[O:17][C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1.C(=O)([O-])[O-].[Na+].[Na+].O>CN(C=O)C>[F:15][C:16]([F:27])([F:28])[O:17][C:18]1[CH:23]=[CH:22][C:21]([C:2]2[CH:3]=[CH:4][C:5]3[N:6]([C:8]([C:11]([F:14])([F:13])[F:12])=[N:9][N:10]=3)[CH:7]=2)=[CH:20][CH:19]=1

参加物

6

反応物 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 27343864-(Trifluoromethoxy)phenylboronic acidHCID 581189066-Bromo-3-(trifluoromethyl)-(1,2,4)triazolo(4,3-a)pyridine

生成物 1

HCID 58118983GS-458967

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

In a 100 mL round-bottom flask 6-bromo-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine (2.124 g), 4-trifluoromethoxyphenylboronic acid (2.466 g), and sodium carbonate (0.635 g) were suspended in a mixture of DMF (81 mL) and deionized water (9 mL) that was degassed with nitrogen. Tetrakis(triphenylphosphine) palladium (0.462 g) was added and the reaction mixture stirred at 90° C. overnight, concentrated, the residue dissolved in ethyl acetate, and washed with water (2×) and concentrated NaHCO3. The combined organic phase dried over MgSO4 and concentrated, then subjected to gradient chromatography (ethyl acetate/hexane) to produce dark grey solid. The solid was recrystallized from ethyl acetate/hexanes mixture to produce off-white material.

後処理

  1. customwas degassed with nitrogen
  2. additionTetrakis(triphenylphosphine) palladium (0.462 g) was added
  3. concentrationconcentrated
  4. dissolutionthe residue dissolved in ethyl acetate
  5. washwashed with water (2×) and concentrated NaHCO3
  6. dry with materialThe combined organic phase dried over MgSO4
  7. concentrationconcentrated
  8. customto produce dark grey solid
  9. customThe solid was recrystallized from ethyl acetate/hexanes mixture
  10. customto produce off-white material

出典と根拠

ORDレコード
ord-590ffb9bb860431cafec21a116e23d1d
出典データセット
uspto-grants-2014_06
特許番号
US08754103B2

関連ノート

読み込み中…