Potassium Carbonate → N-[(3-fluorophenyl)-methyl]-2-(2-methoxy-ethoxy)-4-methyl-7-(trifluoro-methyl)-quinoline-3-carboxylic acid amide

HRID 242121Notes

Reaction equation

HRID 242121 reaction equation
C([O-])([O-])=O.[K+].[K+].[F:7][C:8]1[CH:9]=[C:10]([CH:31]=[CH:32][CH:33]=1)[CH2:11][NH:12][C:13]([C:15]1[C:16]([OH:30])=[N:17][C:18]2[C:23]([C:24]=1[CH3:25])=[CH:22][CH:21]=[C:20]([C:26]([F:29])([F:28])[F:27])[CH:19]=2)=[O:14].Br[CH2:35][CH2:36][O:37][CH3:38].CCOC(C)=O.CCCCCC>CS(C)=O.O.CCOC(C)=O>[F:7][C:8]1[CH:9]=[C:10]([CH2:11][NH:12][C:13]([C:15]2[C:16]([O:30][CH2:35][CH2:36][O:37][CH3:38])=[N:17][C:18]3[C:23]([C:24]=2[CH3:25])=[CH:22][CH:21]=[C:20]([C:26]([F:27])([F:28])[F:29])[CH:19]=3)=[O:14])[CH:31]=[CH:32][CH:33]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 809722-Bromoethyl methyl etherHCID 21226206Ethyl acetate hexaneHCID 178429293HCID 178429293, compound

Product 1

HCID 56848231N-[(3-fluorophenyl)-methyl]-2-(2-methoxy-ethoxy)-4-methyl-7-(trifluoro-methyl)-quinoline-3-carboxylic acid amideYield 25%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

120 mg (0.9 mmol) K2CO3 was added to a solution of 300 mg (0.8 mmol) N-(3-fluorobenzyl)-2-hydroxy-4-methyl-7-(trifluoromethyl)quinoline-3-carboxylic acid amide in DMSO (10 ml) and the solution was stirred for 60 min at RT. 121 mg (0.9 mmol) 1-bromo-2-methoxy-ethane was then added and the RS was stirred for 16 h at RT and thereafter for 72 h at 50° C. It was then diluted with water and EtOAc. The organic phase was separated, washed with brine, dried over MgSO4 and concentrated in a vacuum. After CC (EtOAc/hexane 1:3) of the residue, 72 mg (0.2 mmol, 21%) N-[(3-fluorophenyl)-methyl]-2-(2-methoxy-ethoxy)-4-methyl-7-(trifluoro-methyl)-quinoline-3-carboxylic acid amide (example 7) was obtained. MS: m/z 437.1 [M+H]+.

Workup

  1. stirringthe RS was stirred for 16 h at RT
  2. waitfor 72 h at 50° C
  3. customThe organic phase was separated
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in a vacuum

Sources & evidence

ORD record
ord-a8eb3196e1e94bb0b846c408c9e51028
Source dataset
uspto-grants-2014_02
Patent number
US08653101B2

Reaction notes

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