Allyl iodide → 2-(Allyloxy)-4-(3-fluorophenyl)-6-methoxyquinoline-3-carbonitrile

HRID 640718Notes

Reaction equation

HRID 640718 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([O:18][CH3:19])[CH:16]=3)[NH:11][C:10](=[O:20])[C:9]=2[C:21]#[N:22])[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].[CH2:25](I)[CH:26]=[CH2:27]>CN(C)C=O>[CH2:27]([O:20][C:10]1[C:9]([C:21]#[N:22])=[C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=2)[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([O:18][CH3:19])[CH:16]=2)[N:11]=1)[CH:26]=[CH2:25]

Participants

5

Reactant 3

HCID 11166Allyl iodideHCID 24758Sodium hydrideHCID 114151654-(3-Fluorophenyl)-6-methoxy-2-oxo-1,2-dihydroquinoline-3-carbonitrile

Product 1

HCID 114048472-(Allyloxy)-4-(3-fluorophenyl)-6-methoxyquinoline-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(3-fluorophenyl)-6-methoxy-2-oxo-1,2-dihydroquinoline-3-carbonitrile (1.00 g, 3.40 mmol) in 20 mL of N,N-dimethylformamide at 0° C. was added sodium hydride (163 mg of 60% dispersion in mineral oil, 4.08 mmol). After 30 minutes, allyl iodide was added (0.342 mL, 3.74 mmol), and the reaction was stirred for 2 hours. The reaction was quenched with water and partitioned between EtOAc and water, and the organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude residue was subjected to flash chomatography through SiO2 (5-60% EtOAc/hexane) to provide the second eluting product as the titled compound. 1H NMR, difference nOe, and HMQC NMR spectral data for the product were consistent with the titled compound. ESI+ MS: 335.1 [M+H]+.

Workup

  1. customThe reaction was quenched with water
  2. custompartitioned between EtOAc and water
  3. washthe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-20b30a7b552c40d2a652fd6f80353e4c
Source dataset
uspto-grants-2010_04
Patent number
US07692017B2

Reaction notes

Loading…