Cesium carbonate → Ethyl 8-chloro-1-[(6'-methyl-2,3'-bipyridin-5-yl)methyl]-4-oxo-1,4-dihydrocinnoline-3-carboxylate

HRID 242014Notes

Reaction equation

HRID 242014 reaction equation
Br[C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][C:17]=3[Cl:19])[C:12](=[O:20])[C:11]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[N:10]2)=[CH:4][CH:3]=1.[CH3:26][C:27]1[N:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.O.[Cu]Cl.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P([C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[Cl:19][C:17]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:18]=1[N:9]([CH2:8][C:5]1[CH:4]=[CH:3][C:2]([C:30]3[CH:31]=[N:32][C:27]([CH3:26])=[CH:28][CH:29]=3)=[N:7][CH:6]=1)[N:10]=[C:11]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:12]2=[O:20]

Participants

9

Reactant 3

HCID 10796Cesium carbonateHCID 27630812-Methylpyridine-5-boronic acidHCID 86659998Ethyl 1-[(6-bromopyridin-3-yl)methyl]-8-chloro-4-oxo-1,4-dihydrocinnoline-3-carboxylate

Product 1

HCID 86659999Ethyl 8-chloro-1-[(6'-methyl-2,3'-bipyridin-5-yl)methyl]-4-oxo-1,4-dihydrocinnoline-3-carboxylate

Reagents, catalysts & solvents 5

HCID 62652Cuprous chlorideCatalystHCID 167845palladium(II) acetateCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Ethyl 1-[(6-bromopyridin-3-yl)methyl]-8-chloro-4-oxo-1,4-dihydrocinnoline-3-carboxylate (0.21 g, 0.49 mmol) was combined with (6-methylpyridin-3-yl)boronic acid (0.19 g, 1.2 mmol, 2.5 equiv), copper(I) chloride (48 mg, 0.49 mmol, 1 equiv), cesium carbonate (0.32 g, 0.97 mmol, 2 equiv), palladium(II) acetate (11 mg, 0.049 mmol, 0.1 equiv), and bis(diphenylphosphino)ferrocene (27 mg, 0.049 mmol, 0.1 equiv) in degassed N,N-dimethylformamide (3 mL). The mixture was placed into an oil bath preheated at 95° C. for 15 minutes, cooled to ambient temperature, diluted with water (5 mL) and extracted with ethyl acetate (3×30 mL). The combined organic extracts were washed once with water and brine, dried with sodium sulfate, filtered and concentrated in vacuo, providing the titled compound.

Workup

  1. customThe mixture was placed into an oil bath
  2. extractionextracted with ethyl acetate (3×30 mL)
  3. washThe combined organic extracts were washed once with water and brine
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-41181c222e154a14ad084e8b26daf14d
Source dataset
uspto-grants-2014_02
Patent number
US08653079B2

Reaction notes

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