Methyl iodide → 3-[Methoxy(Phenyl)Methyl]-4-Phenyl-8-(Trifluoromethyl)Quinoline

HRID 2104493Notes

Reaction equation

HRID 2104493 reaction equation
[C:1]1([CH:7]([C:9]2[CH:10]=[N:11][C:12]3[C:17]([C:18]=2[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:16][CH:15]=[CH:14][C:13]=3[C:25]([F:28])([F:27])[F:26])[OH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].I[CH3:32]>CN(C=O)C>[CH3:32][O:8][CH:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:9]1[CH:10]=[N:11][C:12]2[C:17]([C:18]=1[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)=[CH:16][CH:15]=[CH:14][C:13]=2[C:25]([F:28])([F:26])[F:27]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 11222693Phenyl[4-Phenyl-8-(Trifluoromethyl)Quinolin-3-yl]Methanol

Product 1

HCID 669142423-[Methoxy(Phenyl)Methyl]-4-Phenyl-8-(Trifluoromethyl)QuinolineYield 75.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Phenyl[4-phenyl-8-(trifluoromethyl)quinolin-3-yl]methanol (Example 34, 0.05 g, 0.132 mmol) was taken into DMF (3 mL). Next, NaH (0.011 g, 0.264 mmol, 60% dispersion) was added and stirred for 1 hour at room temperature. Next, iodomethane (0.04 ml, 0.66 mmol) was added and allowed to stir for 30 minutes. The reaction was quenched with water then extracted with ether. The combined organics were dried over magnesium sulfate and concentrated. The resulting material was purified via column chromatography using 5% ethyl acetate in hexane as the eluent to yield 0.039 g (75%) of desired product as a white solid. MS (ESI) m/z 394 ([M+H]+); Anal. Calcd for C24H18F3NO: C, 73.27; H, 4.61; N, 3.56. Found: C, 73.15; H, 4.16; N, 3.41.

Workup

  1. stirringto stir for 30 minutes
  2. customThe reaction was quenched with water
  3. extractionthen extracted with ether
  4. dry with materialThe combined organics were dried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe resulting material was purified via column chromatography

Sources & evidence

ORD record
ord-8db5721831b247498a55bbdbac0508ed
Source dataset
uspto-grants-2009_08
Patent number
US07576215B2

Reaction notes

Loading…