Cesium carbonate → HCID 89500826, compound

HRID 2178522Notes

Reaction equation

HRID 2178522 reaction equation
Br[C:2]1[C:7]([CH:8]=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[NH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][C:11]1=[O:16].C(=O)([O-])[O-].[Cs+].[Cs+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1>[O:16]=[C:11]1[CH2:12][CH2:13][CH2:14][CH2:15][N:10]1[C:2]1[C:7]([CH:8]=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 126652-PiperidoneHCID 47149512-Bromonicotinaldehyde

Product 1

HCID 89500826HCID 89500826, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Conditions

Temperature
120 °C

Procedure

2-Bromopyridine-3-carbaldehyde a4-0 (0.5 g, 2.7 mmol, 1 eq) is dissolved in dry and degassed 1,4-dioxane (15 ml). Piperidin-2-one (0.4 g, 4.03 mmol, 1.5 eq), 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (0.31 g, 0.538 mmol, 0.2 eq), tris(dibenzylideneacetone)dipalladium(0) (0.123 g, 0.134 mmol, 0.05 eq) and cesium carbonate (1.752 g, 5.376 mmol, 2 eq) are added. The mixture is heated in a sealed tube in a microwave oven at 120° C. for 45 min. The resulting suspension is filtered over celite and the celite washed with 1,4-dioxane. The filtrate is evaporated under reduced pressure. The residue is then dispersed in ethyl acetate, sonicated, filtered and the filtrate is evaporated under reduced pressure to afford 1.1 g of crude 2-(2-oxopiperidin-1-yl)pyridine-3-carbaldehyde a4-1 which is used in the next step without any further purification.

Workup

  1. customin dry
  2. customdegassed 1,4-dioxane (15 ml)
  3. filtrationThe resulting suspension is filtered over celite
  4. washthe celite washed with 1,4-dioxane
  5. customThe filtrate is evaporated under reduced pressure
  6. additionThe residue is then dispersed in ethyl acetate
  7. customsonicated
  8. filtrationfiltered
  9. customthe filtrate is evaporated under reduced pressure

Sources & evidence

ORD record
ord-391c7b28654f481cb038c4d10a4253e0
Source dataset
uspto-grants-2015_06
Patent number
US09067930B2

Reaction notes

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