Methyl iodide → 3-(1-Methoxy-1-Phenylethyl)-4-Phenyl-8-(Trifluoromethyl)Quinoline

HRID 2104498Notes

Reaction equation

HRID 2104498 reaction equation
[C:1]1([C:7]([C:10]2[CH:11]=[N:12][C:13]3[C:18]([C:19]=2[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:17][CH:16]=[CH:15][C:14]=3[C:26]([F:29])([F:28])[F:27])([OH:9])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].I[CH3:33]>CN(C=O)C>[CH3:33][O:9][C:7]([C:10]1[CH:11]=[N:12][C:13]2[C:18]([C:19]=1[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)=[CH:17][CH:16]=[CH:15][C:14]=2[C:26]([F:29])([F:27])[F:28])([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH3:8]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 113498961-Phenyl-1-[4-phenyl-8-(trifluoromethyl)quinolin-3-yl]ethanol

Product 1

HCID 669131893-(1-Methoxy-1-Phenylethyl)-4-Phenyl-8-(Trifluoromethyl)Quinoline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-Phenyl-1-[4-phenyl-8-(trifluoromethyl)quinolin-3-yl]ethanol (Example 39, 0.096 g, 0.243 mmol) was taken into DMF (3 mL) then NaH (0.020 g, 0.487 mmol) was added and stirred for 20 minutes. Lastly, iodomethane (0.08 mL, 1.22 mmol) was added and stirring was continued for 30 minutes. The reaction was quenched with water and 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. MS (ESI) m/z 408 ([M+H]+); 1H NMR (CDCl3) δ 9.59 (s, 1H), 8.01 (d, J=6.8 Hz, 1H), 7.31 (m, 3H), 7.12 (m, 5H), 7.0 (m, 2H), 6.74 (dd, J=7.5 and 1.2 Hz, 1H), 6.63 (dd, J=7.7 and 1.3 Hz, 1H), 3.06 (s, 3H), 1.8 (s, 3H).

Workup

  1. stirringstirring
  2. waitwas continued for 30 minutes
  3. customThe reaction was quenched with water
  4. extractionextracted with ether
  5. dry with materialThe combined organics were dried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe resulting material was purified via column chromatography

Sources & evidence

ORD record
ord-4b8eeb439e5949cb8c8515e2b8b70e0c
Source dataset
uspto-grants-2009_08
Patent number
US07576215B2

Reaction notes

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