Dimethyl malonate → HCID 86719107, compound

HRID 572925Notes

Reaction equation

HRID 572925 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][N:3]=1.[C:9]([O:16][CH3:17])(=[O:15])[CH2:10][C:11]([O:13][CH3:14])=[O:12].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.[Cu]I>[F:8][C:5]1[CH:6]=[CH:7][C:2]([CH:10]([C:9]([O:16][CH3:17])=[O:15])[C:11]([O:13][CH3:14])=[O:12])=[N:3][CH:4]=1

Participants

6

Reactant 3

HCID 7943Dimethyl malonateHCID 10796Cesium carbonateHCID 27831712-Bromo-5-fluoropyridine

Product 1

HCID 86719107HCID 86719107, compoundYield 31%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Procedure

The solution of 2-bromo-5-fluoropyridine (1.0 g, 5.68 mmol), dimethyl malonate (3.0 g, 22.7 mmol) picolinic acid (559.6 mg, 4.54 mmol), CuI (431.8 mg, 2.27 mmol) and Cs2CO3 (5.6 g, 17.05 mmol) in DMF (30 mL) was stirred at 100 degree for 12 h. After cooling to room temperature, the reaction mixture was filtered, diluted with H2O and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate and evaporated under reduced pressure. The residue was purified by a standard method to give desired compound (400 mg). LC-MS: m/z (M+H)=228.2

Workup

  1. filtrationthe reaction mixture was filtered
  2. additiondiluted with H2O
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated under reduced pressure
  7. customThe residue was purified by a standard method

Sources & evidence

ORD record
ord-c309d7c2052e489396f01169e114d14d
Source dataset
uspto-grants-2015_05
Patent number
US09029531B2

Reaction notes

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