Methyl iodide → HCID 56848282, compound

HRID 242124Notes

Reaction equation

HRID 242124 reaction equation
[C:1]([O-:4])([O-])=O.[K+].[K+].CI.[CH2:9]([O:11][C:12]1[C:21]([C:22]([NH:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[CH:27]=2)=[O:23])=[C:20](O)[C:19]2[C:14](=[CH:15][C:16]([C:34]([F:37])([F:36])[F:35])=[CH:17][CH:18]=2)[N:13]=1)[CH3:10].CCOC(C)=O.CCCCCC>CN(C=O)C.O>[CH2:9]([O:11][C:12]1[C:21]([C:22]([NH:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[CH:27]=2)=[O:23])=[C:20]([O:4][CH3:1])[C:19]2[C:14](=[CH:15][C:16]([C:34]([F:36])([F:37])[F:35])=[CH:17][CH:18]=2)[N:13]=1)[CH3:10]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 21226206Ethyl acetate hexaneHCID 178467384HCID 178467384, compound

Product 1

HCID 56848282HCID 56848282, compoundYield 85.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

300 mg (2.2 mmol) K2CO3 and 0.9 ml (14.6 mmol) methyliodide were added to a solution of 300 mg (0.7 mmol) 2-ethoxy-N-(3-fluorobenzyl)-4-hydroxy-7-(trifluoro-methyl)quinoline-3-carboxylic acid amide in DMF (5 ml) and the mixture was stirred for 16 h at RT. The mixture was subsequently diluted with water and extracted with EtOAc. The organic phase was washed with water and brine, dried over Na2SO4 and concentrated in a vacuum. After CC (EtOAc/hexane 1:12) of the residue, 240 mg (0.6 mmol, 81%) 2-ethoxy-N-[(3-fluorophenyl)-methyl]-4-methoxy-7-(trifluoromethyl)-quinoline-3-carboxylic acid amide (example 12) was obtained. MS: m/z 423.1 [M+H]+.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic phase was washed with water and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in a vacuum

Sources & evidence

ORD record
ord-ab6113894fe843038bd81a5275d7ef65
Source dataset
uspto-grants-2014_02
Patent number
US08653101B2

Reaction notes

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