Sodium Iodide → HCID 86675785, 화합물

HRID 69084

반응식

HRID 69084 반응식
[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

참가 물질

7

반응물 4

HCID 5238Sodium IodideHCID 81531DiisopropylethylamineHCID 170397906-Bromo-2-chloro-3-(chloromethyl)quinolineHCID 178516143HCID 178516143, 화합물

생성물 1

HCID 86675785HCID 86675785, 화합물

시약·촉매·용매 2

HCID 962Water용매HCID 180504Ceric ammonium nitrate용매

반응 조건

온도
70 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-2ba94ad31aea429aaca5434b4d9dc5cd
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822485B2

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