Cesium carbonate → HCID 86653283, compound

HRID 2389273Notes

Reaction equation

HRID 2389273 reaction equation
Cl[C:2]1[CH:7]=[C:6]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][C:15]3[CH:16]=[C:17]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[C:18](=[O:25])[N:19]4[C:24]=3[CH:23]=[CH:22][CH:21]=[CH:20]4)[CH2:10][CH2:9]2)[CH:5]=[CH:4][N:3]=1.[CH:31]([B-](F)(F)F)=[CH2:32].[K+].C(=O)([O-])[O-].[Cs+].[Cs+]>C1COCC1.CCOC(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>[O:25]=[C:18]1[N:19]2[C:24]([CH:23]=[CH:22][CH:21]=[CH:20]2)=[C:15]([CH2:14][N:11]2[CH2:12][CH2:13][N:8]([C:6]3[CH:5]=[CH:4][N:3]=[C:2]([CH:31]=[CH2:32])[CH:7]=3)[CH2:9][CH2:10]2)[CH:16]=[C:17]1[C:26]([O:28][CH2:29][CH3:30])=[O:27]

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 23679353Potassium vinyltrifluoroborateHCID 58256242HCID 58256242, compound

Product 1

HCID 86653283HCID 86653283, compound

Reagents, catalysts & solvents 3

HCID 178418851HCID 178418851, compoundCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
130 °C

Procedure

To a solution of ethyl 1-{[4-(2-chloropyridin-4-yl)piperazin-1-yl]methyl}-4-oxo-4H-quinolizine-3-carboxylate (0.500 g, 1.17 mmol), potassium vinyltrifluoroborate (0.471 g, 3.51 mmol), and 1N cesium carbonate (2.34 mL, 2.34 mmol) in 5 mL of THF under nitrogen was added bis(tri-tert-butyl-phosphine)palladium(0) (10 mol %). The reaction mixture was stirred at 130° C. for 5 hours, then cooled to room temperature. The mixture was diluted with EtOAc and washed with aqueous sodium bicarbonate and brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography eluting with 0-5% MeOH in DCM to provide ethyl 4-oxo-1-{[4-(2-vinylpyridin-4-yl)piperazine-1-yl]methyl}-4H-quinolizine-3-carboxylate that gave a mass ion (ES+) of 419.0 for M+H+.

Workup

  1. temperaturecooled to room temperature
  2. washwashed with aqueous sodium bicarbonate and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel chromatography
  7. washeluting with 0-5% MeOH in DCM

Sources & evidence

ORD record
ord-afbf174848234e4d9e69dd71f35620a4
Source dataset
uspto-grants-2012_09
Patent number
US08273737B2

Reaction notes

Loading…