Sodium Iodide → HCID 86675785, compound

HRID 69084

Reaction equation

HRID 69084 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

HCID 86675785HCID 86675785, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 180504Ceric ammonium nitrateSolvent

Conditions

Temperature
70 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-2ba94ad31aea429aaca5434b4d9dc5cd
Source dataset
uspto-grants-2014_09
Patent number
US08822485B2

Linked notes

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