Propionamide → HCID 90410860, compound

HRID 626512Notes

Reaction equation

HRID 626512 reaction equation
Cl[C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:10]=[N:11][C:12]([N+:15]([O-:17])=[O:16])=[CH:13][CH:14]=2)[CH:5]=[CH:4][N:3]=1.[C:18]([NH2:22])(=[O:21])[CH2:19][CH3:20].C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2].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]>[N+:15]([C:12]1[N:11]=[CH:10][C:9]([O:8][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH:22][C:18](=[O:21])[CH2:19][CH3:20])[CH:7]=2)=[CH:14][CH:13]=1)([O-:17])=[O:16]

Participants

7

Reactant 3

HCID 6578PropionamideHCID 10796Cesium carbonateHCID 593227792-Chloro-4-((6-nitropyridin-3-yl)oxy)pyridine

Product 1

HCID 90410860HCID 90410860, compoundYield 45%

Reagents, catalysts & solvents 3

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
95 °C

Procedure

A solution of Example A1 (1.0 g, 3.97 mmol) in dioxane (20 mL) was sparged with Ar, treated with propionamide (0.581 g, 7.95 mmol) and Cs2CO3 (1.942 g, 5.96 mmol), sparged with, treated with dppf (12.38 g, 22.33 mmol) and Pd2(dba)3 (0.182 g, 0.199 mmol), sparged once again with Ar and heated at 95° C. overnight. Pd(dppf)2Cl2.DCM (50 mg) was added and the mixture heated at 95° C. for 4 h. The mixture was cooled to RT, treated with EtOAc and the solids removed via filtration through silica gel. The filtrate was concentrated to dryness and purified twice via silica gel chromatography (MeOH/DCM) to afford N-(4-((6-nitropyridin-3-yl)oxy)pyridin-2-yl)propionamide (513 mg, 45%). MS (ESI) m/z: 289.1 (M+H+).

Workup

  1. customsparged with,
  2. customsparged once again with Ar
  3. additionDCM (50 mg) was added
  4. temperaturethe mixture heated at 95° C. for 4 h
  5. temperatureThe mixture was cooled to RT
  6. additiontreated with EtOAc
  7. customthe solids removed via filtration through silica gel
  8. concentrationThe filtrate was concentrated to dryness
  9. custompurified twice via silica gel chromatography (MeOH/DCM)

Sources & evidence

ORD record
ord-7b9a737986f843ceb558ee1459b7950e
Source dataset
uspto-grants-2016_04
Patent number
US09309224B2

Reaction notes

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