Sodium borohydride → Methyl 3-[4-(5-aminopyridin-2-ylsulfanyl)phenyl]propionate

HRID 884105Notes

Reaction equation

HRID 884105 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([S:10][C:11]2[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])=[CH:13][CH:12]=2)=[N:8][CH:9]=1)([O-])=O.[BH4-].[Na+]>CO.[C].[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([S:10][C:11]2[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])=[CH:13][CH:12]=2)=[N:8][CH:9]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 68525632Methyl 3-[4-(5-nitropyridin-2-ylsulfanyl)phenyl]propionate

Product 1

HCID 68526023Methyl 3-[4-(5-aminopyridin-2-ylsulfanyl)phenyl]propionate

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of methyl 3-[4-(5-nitropyridin-2-ylsulfanyl)phenyl]propionate (2.97 g, 9.33 mmol) in methanol (50 mL) were added sodium borohydride (0.590 g, 15.6 mmol) and 10% palladium-carbon (1.80 g), and the resulting solution was stirred for 24 hours at room temperature under a hydrogen atmosphere at atmospheric pressure. The reaction solution was filtered through Celite, and to the resulting filtrate was added concentrated hydrochloric acid (1.5 mL), and concentrated under reduced pressure. To the residue was added a saturated sodium bicarbonate solution, and extracted with ethyl acetate, and the ethyl acetate layer was washed with brine. The ethyl acetate layer was dried over anhydrous magnesium sulfate, and evaporated, to thereby yield 2.49 g of the title compound.

Workup

  1. filtrationThe reaction solution was filtered through Celite
  2. additionto the resulting filtrate was added concentrated hydrochloric acid (1.5 mL)
  3. concentrationconcentrated under reduced pressure
  4. additionTo the residue was added a saturated sodium bicarbonate solution
  5. extractionextracted with ethyl acetate
  6. washthe ethyl acetate layer was washed with brine
  7. dry with materialThe ethyl acetate layer was dried over anhydrous magnesium sulfate
  8. customevaporated

Sources & evidence

ORD record
ord-799e0954f1aa464c955709c00ba60b78
Source dataset
uspto-grants-2012_08
Patent number
US08236826B2

Reaction notes

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