Dimethylformamide → HCID 67772977, compound

HRID 533401Notes

Reaction equation

HRID 533401 reaction equation
Br[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:6]=[N:7]2.[F:17][C:18]1[CH:23]=[C:22]([F:24])[CH:21]=[C:20]([F:25])[C:19]=1OB(O)O.[F-].[Cs+].CN(C=O)C>O.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C.[Ag]=O>[F:17][C:18]1[CH:23]=[C:22]([F:24])[CH:21]=[C:20]([F:25])[C:19]=1[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:6]=[N:7]2

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 25953Cesium fluorideHCID 22237819HCID 22237819, compoundHCID 67773468Ethyl 5-bromoquinoline-3-carboxylate

Product 1

HCID 67772977HCID 67772977, compoundYield 44.9%

Reagents, catalysts & solvents 3

HCID 92152Silver(II) oxideCatalystHCID 178418851HCID 178418851, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

Under argon gas atmosphere, a mixture of ethyl 5-bromoquinoline-3-carboxylate (113 mg), 2,4,6-trifluorophenylboric acid (106 mg), bis(tri-t-butylphosphine)palladium (41 mg), cesium fluoride (123 mg), silver oxide (112 mg), and DMF (2 mL) was heated under stirring in an oil bath at 100° C. for 15 hours. The reaction liquid was returned to room temperature, diluted with water, and then extracted with ethyl acetate. The organic layer was concentrated under reduced pressure, and the resulting residue was purified under silica gel column chromatography (hexane/ethyl acetate) to obtain ethyl 5-(2,4,6-trifluorophenyl)quinoline-3-carboxylate (60 mg).

Workup

  1. temperaturewas heated
  2. customThe reaction liquid
  3. customwas returned to room temperature
  4. extractionextracted with ethyl acetate
  5. concentrationThe organic layer was concentrated under reduced pressure
  6. customthe resulting residue was purified under silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-26febdbc860b4a37a39ff6e4ab8d40fc
Source dataset
uspto-grants-2014_10
Patent number
US08853242B2

Reaction notes

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