methyl 2-(7-bromo-2-oxoquinolin-1(2H)-yl)acetate → methyl 2-(7-cyano-2-oxoquinolin-1(2H)-yl)acetate

HRID 1519799Notes

Reaction equation

HRID 1519799 reaction equation
[C:1]([Cu])#[N:2].Br[C:5]1[CH:14]=[C:13]2[C:8]([CH:9]=[CH:10][C:11](=[O:20])[N:12]2[CH2:15][C:16]([O:18][CH3:19])=[O:17])=[CH:7][CH:6]=1>CN(C=O)C.CCOCC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]([C:5]1[CH:14]=[C:13]2[C:8]([CH:9]=[CH:10][C:11](=[O:20])[N:12]2[CH2:15][C:16]([O:18][CH3:19])=[O:17])=[CH:7][CH:6]=1)#[N:2]

Participants

6

Reactant 2

HCID 68784498methyl 2-(7-bromo-2-oxoquinolin-1(2H)-yl)acetateHCID 178418546HCID 178418546, compound

Product 1

HCID 68785451methyl 2-(7-cyano-2-oxoquinolin-1(2H)-yl)acetateYield 71.4%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

CuCN (0.211 g, 2.36 mmol) and Pd(PPh3)4 (0.136 g, 0.118 mmol) were added to a solution of methyl 2-(7-bromo-2-oxoquinolin-1(2H)-yl)acetate (0.35 g, 1.18 mmol) in DMF (1 mL) in a screw cap vial. The vial was sealed and placed into a oil bath at 120° C. and the reaction mixture was stirred for 18 h. The resulting mixture was diluted with Et2O and washed with brine. The organic phase was separated, dried (Na2SO4), filtered, concentrated under vacuum and the residue was purified on a silica gel column to give methyl 2-(7-cyano-2-oxoquinolin-1(2H)-yl)acetate (0.204 g, 71%). Retention time (min)=1.464, method [1], MS(ESI) 243.1 (M+H).

Workup

  1. customcap vial
  2. customThe vial was sealed
  3. customplaced into a oil bath at 120° C.
  4. washwashed with brine
  5. customThe organic phase was separated
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. customthe residue was purified on a silica gel column

Sources & evidence

ORD record
ord-d27de851483b459f958e577ebd394a95
Source dataset
uspto-grants-2015_07
Patent number
US09073891B2

Reaction notes

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