Sodium Bicarbonate → HCID 58978986, compound

HRID 1181030Notes

Reaction equation

HRID 1181030 reaction equation
[C:1]1([C:7]2[CH:15]=[CH:14][C:10]([C:11]([NH2:13])=[S:12])=[CH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:16][O:17][C:18](=[O:25])[CH2:19][C:20](=O)[CH:21](Br)[CH3:22].C([O-])(O)=O.[Na+]>O1CCOCC1>[CH3:16][O:17][C:18](=[O:25])[CH2:19][C:20]1[N:13]=[C:11]([C:10]2[CH:9]=[N:8][C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[CH:15][CH:14]=2)[S:12][C:21]=1[CH3:22]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 9815681Methyl 4-bromo-3-oxopentanoateHCID 17984629HCID 17984629, compound

Product 1

HCID 58978986HCID 58978986, compoundYield 56.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 6-phenyl-thionicotinamide (7.0 g) and 4-bromo-3-oxo-pentanoic acid methyl ester (9.15 g, 35 mmol) in 1,4-dioxane (30 mL) was heated at reflux for 4 h. The reaction mixture was cooled, poured into aqueous saturated NaHCO3, and extracted with CH2Cl2. The organic layer was dried (MgSO4), filtered, and concentrated. The residue was purified by silica gel chromatography (hexanes/EtOAc, 2/1) to afford the title compound (6.0 g, 56%). MS (ESI) m/z 325 (M+H)+.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 h
  3. temperatureThe reaction mixture was cooled
  4. extractionextracted with CH2Cl2
  5. dry with materialThe organic layer was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel chromatography (hexanes/EtOAc, 2/1)

Sources & evidence

ORD record
ord-efb17c77c02c4d13ab6a537a182243a6
Source dataset
uspto-grants-2007_10
Patent number
US07282501B2

Reaction notes

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