Cesium carbonate → HCID 86645056, compound

HRID 2380868Notes

Reaction equation

HRID 2380868 reaction equation
Br[C:2]1[C:3]([C:8]2([C:31]#[N:32])[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)=[N:4][CH:5]=[CH:6][CH:7]=1.[CH:33]([B-](F)(F)F)=[CH2:34].[K+].C(=O)([O-])[O-].[Cs+].[Cs+]>C1COCC1.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>[C:31]([C:8]1([C:3]2[C:2]([CH:33]=[CH2:34])=[CH:7][CH:6]=[CH:5][N:4]=2)[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:16]=[C:17]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[C:18](=[O:25])[N:19]3[C:24]=2[CH:23]=[CH:22][CH:21]=[CH:20]3)[CH2:10][CH2:9]1)#[N:32]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 23679353Potassium vinyltrifluoroborateHCID 86645057HCID 86645057, compound

Product 1

HCID 86645056HCID 86645056, compound

Reagents, catalysts & solvents 2

HCID 178418851HCID 178418851, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
160 °C

Procedure

In a 2-5 mL Emrys™ process vial, the ethyl 1-{[4-(3-bromopyridin-2-yl)-4-cyanopiperidin-1-yl]methyl}-4-oxo-4H-quinolizine-3-carboxylate (50 mg, 0.10 mmol) was dissolved in 0.40 mL of anhydrous THF and treated with potassium vinyltrifluoroborate (40.6 mg, 0.30 mmol) and 1M cesium carbonate solution (0.20 mL, 0.20 mmol). The reaction was purged with a stream of nitrogen, charged with bis(tri-tert-butylphosphine)palladium(0) (5.2 mg, 0.010 mmol), and heated via Emrys Optimizer™ microwave to 160° C. for 10 minutes. Filtration and solvent removal provided material, which was subjected to preparative reverse phase HPLC. Collection of product containing fractions and removal of solvent afforded the ethyl 1-{[4-cyano-4-(3-vinylpyridin-2-yl)piperidin-1-yl]methyl}-4-oxo-4H-quinolizine-3-carboxylate.

Workup

  1. customThe reaction was purged with a stream of nitrogen
  2. filtrationFiltration and solvent removal
  3. customprovided material, which
  4. customCollection of product
  5. additioncontaining
  6. customfractions and removal of solvent

Sources & evidence

ORD record
ord-504b8dc87b7a41868445af9c4387310f
Source dataset
uspto-grants-2012_09
Patent number
US08258135B2

Reaction notes

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