Butyl bromide → HCID 66584541, compound

HRID 242030Notes

Reaction equation

HRID 242030 reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([F:15])([F:14])[F:13])=[CH:9][CH:10]=2)[NH:5][C:4](=[O:16])[C:3]=1[C:17]([O-:19])=[O:18].C([O-])([O-])=O.[K+].[K+].Br[CH2:27][CH2:28][CH2:29][CH3:30].[CH3:31][CH2:32]OC(C)=O.CCCCCC>CS(C)=O.O>[CH2:27]([N:5]1[C:6]2[C:11](=[CH:10][CH:9]=[C:8]([C:12]([F:14])([F:15])[F:13])[CH:7]=2)[C:2]([CH3:1])=[C:3]([C:17]([O:19][CH2:31][CH3:32])=[O:18])[C:4]1=[O:16])[CH2:28][CH2:29][CH3:30]

Participants

7

Reactant 4

HCID 8002Butyl bromideHCID 11430Potassium CarbonateHCID 21226206Ethyl acetate hexaneHCID 86662686HCID 86662686, compound

Product 1

HCID 66584541HCID 66584541, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 1.0 g (3.3 mmol) 4-methyl-2-oxo-7-(trifluoromethyl)-1H-quinoline-3-carboxylate (for synthesis see example 1, section a)) in DMSO (9 ml) was treated with 461 mg (3.3 mmol) K2CO3 and 360 μl (3.3 mmol) 1-bromobutane at RT and was subsequently heated at 50° C. for 90 mins. After cooling to RT the RS was diluted with water (30 ml) and extracted with EtOAc (3×50 ml). The combined organic layers were washed with water and brine, dried over Na2SO4 and concentrated in vacuo. After CC (EtOAc/hexane 1:8) of the residue, 480 mg (1.4 mmol, 40%) ethyl 1-butyl-4-methyl-2-oxo-7-(trifluoromethyl)-1H-quinoline-3-carboxylate was obtained.

Workup

  1. temperatureAfter cooling to RT the RS
  2. extractionextracted with EtOAc (3×50 ml)
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-59e014517e674f88a39fef60a0e996fd
Source dataset
uspto-grants-2014_02
Patent number
US08653102B2

Reaction notes

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