Water → HCID 66913947, compound

HRID 2104613Notes

Reaction equation

HRID 2104613 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Br[CH2:11][C:12]1[CH:13]=[N:14][C:15]2[C:20]([C:21]=1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[CH:19][CH:18]=[CH:17][C:16]=2[C:28]([F:31])([F:30])[F:29].O>CN(C=O)C>[O:7]([CH2:11][C:12]1[CH:13]=[N:14][C:15]2[C:20]([C:21]=1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[CH:19][CH:18]=[CH:17][C:16]=2[C:28]([F:31])([F:29])[F:30])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 996PhenolHCID 24758Sodium hydrideHCID 66913569HCID 66913569, compound

Product 1

HCID 66913947HCID 66913947, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of phenol (235 mg, 5.0 mmol) in DMF (2.0 mL) is treated with NaH (60% in oil, 100 mg, 2.5 mmol) for 20 min and then treated with 3-(bromomethyl)-4-phenyl-8-(trifluoromethyl)quinoline (183 mg, 0.50 mmol) in DMF (1.0 mL). After 16 h, the reaction is treated with water and extracted with ether. The extract is dried with MgSO4 and concentrated to an oil. Chromatography with 10:90 ethyl acetate:hexane affords the title compound as a white solid (114 mg, 62%). MS (ES) m/z 380.2; HRMS: calcd for C23H16F3NO, 379.1184; found (ESI, [M+H]+), 380.1246;

Workup

  1. extractionextracted with ether
  2. dry with materialThe extract is dried with MgSO4
  3. concentrationconcentrated to an oil

Sources & evidence

ORD record
ord-94d571dad45042bd9f52e8db6c6e279b
Source dataset
uspto-grants-2009_08
Patent number
US07576215B2

Reaction notes

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