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Methyl iodide → 1-(4-(6,7-Dimethoxyquinolin-4-yloxy)-3-fluorophenyl)-4-(methoxy(phenyl)methyl)pyrrolidin-2-one

HRID 1993389
Notes
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Reaction equation

HRID 1993389 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:21]=[CH:20][C:19]([N:22]2[CH2:26][CH:25]([CH:27]([OH:34])[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH2:24][C:23]2=[O:35])=[CH:18][C:17]=1[F:36].[H-].[Na+].[CH3:39]I>C1COCC1.CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:21]=[CH:20][C:19]([N:22]2[CH2:26][CH:25]([CH:27]([O:34][CH3:39])[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH2:24][C:23]2=[O:35])=[CH:18][C:17]=1[F:36]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 587517811-(4-(6,7-Dimethoxyquinolin-4-yloxy)-3-fluorophenyl)-4-(hydroxy(phenyl)methyl)pyrrolidin-2-one

Product 1

HCID 118577281-(4-(6,7-Dimethoxyquinolin-4-yloxy)-3-fluorophenyl)-4-(methoxy(phenyl)methyl)pyrrolidin-2-one

Reagents, catalysts & solvents 1

HCID 21974620
tetrahydrofuran N,N-dimethylformamide
Solvent

Procedure

To a solution of 1-(4-(6,7-dimethoxyquinolin-4-yloxy)-3-fluorophenyl)-4-(hydroxy(phenyl)methyl)pyrrolidin-2-one (Example 48, 0.1 g, 0.2 mmol) in THF/DMF (1 mL:1 mL) was added NaH (0.1 g, 2.5 mmol) solid. The reaction was stirred at RT for 1 h. MeI (0.1 mL, 1.6 mmol) was added via a syringe and the reaction was stirred for 1 h. The reaction was quenched with 10 mL of satd. NH4Cl solution and 10 mL of water. The solution was diluted with 50 mL of EtOAc. The organic phase was separated and was washed with 30 mL of brine, dried over Na2SO4 and concentrated in vacuo. The crude oil was purified by chromatography (10% EtOAc/hexanes to EtOAc) to give colorless film. MS (ESI pos. ion) m/z: 503.5 (M+H). Calc'd Exact Mass for C29H27FN2O5: 502.53.

Workup

  1. stirringthe reaction was stirred for 1 h
  2. customThe reaction was quenched with 10 mL of satd
  3. additionThe solution was diluted with 50 mL of EtOAc
  4. customThe organic phase was separated
  5. washwas washed with 30 mL of brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customThe crude oil was purified by chromatography (10% EtOAc/hexanes to EtOAc)
  9. customto give colorless film

Sources & evidence

ORD record
ord-b56710e1e17a45a6b032a227839e4c85
Source dataset
uspto-grants-2010_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07652009B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes