2-Propanethiol → 2-Isopropylsulfanyl-6-methyl-nicotinic acid methyl ester

HRID 62848

Reaction equation

HRID 62848 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[N:6][C:5]=1Cl.C([O-])([O-])=O.[Cs+].[Cs+].[CH3:19][CH:20]([SH:22])[CH3:21]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[N:6][C:5]=1[S:22][CH:20]([CH3:21])[CH3:19]

Participants

5

Reactant 3

HCID 63642-PropanethiolHCID 10796Cesium carbonateHCID 13055804Methyl 2-chloro-6-methylpyridine-3-carboxylate

Product 1

HCID 901181052-Isopropylsulfanyl-6-methyl-nicotinic acid methyl esterYield 69.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Chloro-6-methyl-nicotinic acid methyl ester (1.39 g, 7.44 mmol) obtained in Step A was dissolved in DMF (15 mL). Cs2CO3(4.88 g, 14.99 mmol) and propane-2-thiol (1.39 mL, 14.99 mmol) were added to the solution, and the mixture was stirred at room temperature for 2 hours. The reactant was concentrated under reduced pressure to remove the solvent. The residue was added with water and then extracted with EtOAc. The organic layer was dried with MgSO4, filtered and concentrated under reduced pressure. The obtained residue was purified by column chromatography (eluent EtOAc/Hex=1/5) to obtain the title compound (1.17 g, 69%).

Workup

  1. concentrationThe reactant was concentrated under reduced pressure
  2. customto remove the solvent
  3. additionThe residue was added with water
  4. extractionextracted with EtOAc
  5. dry with materialThe organic layer was dried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe obtained residue was purified by column chromatography (eluent EtOAc/Hex=1/5)

Sources & evidence

ORD record
ord-7ad44a8f9f314848acf3a650ee093685
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Linked notes

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