Sodium Iodide → HCID 86675785、化合物

HRID 69084

反応式

HRID 69084 の反応式
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([Cl:12])[C:6]([CH2:13]Cl)=[CH:5]2.[F:15][C:16]([F:25])([F:24])[C:17]1[N:22]=[CH:21][N:20]=[C:19]([OH:23])[CH:18]=1.CCN(C(C)C)C(C)C.[I-].[Na+]>O=[N+]([O-])[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[Ce+4].[NH4+].[NH4+].O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([Cl:12])[C:6]([CH2:13][O:23][C:19]1[CH:18]=[C:17]([C:16]([F:25])([F:15])[F:24])[N:22]=[CH:21][N:20]=1)=[CH:5]2

参加物

7

反応物 4

HCID 5238Sodium IodideHCID 81531DiisopropylethylamineHCID 170397906-Bromo-2-chloro-3-(chloromethyl)quinolineHCID 178516143HCID 178516143、化合物

生成物 1

HCID 86675785HCID 86675785、化合物

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 180504Ceric ammonium nitrate溶媒

反応条件

温度
70 °C

実験手順

6-Bromo-2-chloro-3-(chloromethyl)quinoline (0.60 g, 2.1 mmol), 6-(trifluoromethyl)-4-pyrimidinol (0.34 g, 2.1 mmol), DIEA (0.54 ml, 3.1 mmol) and sodium iodide (0.31 g, 2.1 mmol) were suspended in CAN (50 mL) and heated to 70° C. for 1 h. The reaction was cooled, diluted with water (100 mL) and extracted with EtOAc (200 mL). After drying with magnesium sulfate the organic was evaporated to dryness under reduced pressure. Purification using low pressure silica chromatography (0-10% methanol in DCM gradient) to give the desired 6-bromo-2-chloro-3-((6-(trifluoromethyl)pyrimidin-4-yloxy)methyl)quinoline. Step 2 and 3: The product from step 1 was taken through a procedure similar to that described in steps 3 and 4 of Example 9, to provide the titled compound, o-tolyl-3-((6-(trifluoromethyl)pyrimidin-4-yloxy)methyl)quinolin-2-amine. (ESI, pos. ion) m/z: 411 (M+1).

後処理

  1. temperatureThe reaction was cooled
  2. extractionextracted with EtOAc (200 mL)
  3. dry with materialAfter drying with magnesium sulfate the
  4. customorganic was evaporated to dryness under reduced pressure
  5. customPurification

出典と根拠

ORDレコード
ord-2ba94ad31aea429aaca5434b4d9dc5cd
出典データセット
uspto-grants-2014_09
特許番号
US08822485B2

関連ノート

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