Pyridine → 2-Methyl-2-(pyridine-3-sulfonyl)-propionic acid ethyl ester

HRID 545309Notes

Reaction equation

HRID 545309 reaction equation
[Na+].[N:2]1[CH:7]=[CH:6][CH:5]=[C:4]([S:8]([O-:10])=[O:9])[CH:3]=1.N1C=CC=CC=1.Br[C:18]([CH3:25])([CH3:24])[C:19]([O:21][CH2:22][CH3:23])=[O:20]>CN(C=O)C.C(Cl)Cl>[CH2:22]([O:21][C:19](=[O:20])[C:18]([CH3:25])([S:8]([C:4]1[CH:3]=[N:2][CH:7]=[CH:6][CH:5]=1)(=[O:10])=[O:9])[CH3:24])[CH3:23]

Participants

6

Reactant 3

HCID 1049PyridineHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 23697071Sodium pyridine-3-sulfinate

Product 1

HCID 581984122-Methyl-2-(pyridine-3-sulfonyl)-propionic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

The crude 3-pyridylsulfinic acid sodium salt (4.4 mmol, synthesised by variation A) was suspended in DMF (20 mL). Pyridine (0.8 mL) and ethyl α-bromoisobutyrate (1 mL) were added. The reaction was stirred at room temperature under nitrogen for 18 h. The reaction mixture was diluted with DCM (200 mL), washed with water (2×100 mL), brine (1×50 mL) and dried over Na2SO4. Filtration, concentration under reduced pressure, followed by column chromatography (silica, eluent DCM, 0-10% ethyl acetate) afforded 0.24 g of 2-methyl-2-(pyridine-3-sulfonyl)-propionic acid ethyl ester.

Workup

  1. washwashed with water (2×100 mL), brine (1×50 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationFiltration, concentration under reduced pressure

Sources & evidence

ORD record
ord-d4b14861fc8645bc9a62b8fcb912fb41
Source dataset
uspto-grants-2011_05
Patent number
US07935715B2

Reaction notes

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