Diethyl Malonate → HCID 59331284, compound

HRID 1881829Notes

Reaction equation

HRID 1881829 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[O:12][CH2:11][CH2:10][O:9]2)=[N:6][CH:7]=1.[C:13]([O:21][CH2:22][CH3:23])(=[O:20])[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16].C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1C)(C)(C)C.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[O:9]1[CH2:10][CH2:11][O:12][CH:8]1[C:5]1[N:6]=[CH:7][C:2]([CH:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:13]([O:21][CH2:22][CH3:23])=[O:20])=[CH:3][CH:4]=1

Participants

8

Reactant 4

HCID 7761Diethyl MalonateHCID 62657Potassium Phosphate, TribasicHCID 27349372-(Di-tert-butylphosphino)-2'-methyl-1,1'-biphenylHCID 44754838HCID 44754838, compound

Product 1

HCID 59331284HCID 59331284, compoundYield 72%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 5-bromo-2-(1,3-dioxolan-2-yl)pyridine (2.00 g) in 1,4-dioxane (30 mL) were added diethyl malonate (1.6 mL), palladium acetate (II) (195 mg), di-tert-butyl(2′-methylbiphenyl-2-yl)phosphane (600 mg) and tripotassium phosphate (4.30 g), and the mixture was heated under reflux under argon atmosphere overnight. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate, and the insoluble material was filtered off through celite. The filtrate was concentrated, and the residue was subjected to silica gel column chromatography, and the title compound (1.95 g, yield 72%) was obtained as a brown oil from a fraction eluted with ethyl acetate-hexane (1:1, volume ratio). MS: 310 (MH+).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux under argon atmosphere overnight
  3. filtrationthe insoluble material was filtered off through celite
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-568f314b0a4c405b8f3c1cdc36351e66
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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