Pyridine → HCID 58198422, compound

HRID 545321Notes

Reaction equation

HRID 545321 reaction equation
[Na+].[Cl:2][C:3]1[N:8]=[CH:7][C:6]([S:9]([O-:11])=[O:10])=[CH:5][CH:4]=1.N1C=CC=CC=1.Br[C:19]([CH3:26])([CH3:25])[C:20]([O:22][CH2:23][CH3:24])=[O:21]>CN(C=O)C>[CH2:23]([O:22][C:20](=[O:21])[C:19]([S:9]([C:6]1[CH:7]=[N:8][C:3]([Cl:2])=[CH:4][CH:5]=1)(=[O:11])=[O:10])([CH3:26])[CH3:25])[CH3:24]

Participants

5

Reactant 3

HCID 1049PyridineHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 87247012HCID 87247012, compound

Product 1

HCID 58198422HCID 58198422, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

The crude 6-chloro-pyridine-3-sulfinic acid sodium salt (4.7 mmol) was suspended in DMF (20 mL). Pyridine (0.8 mL) and ethyl α-bromoisobutyrate (1 mL) were added. The reaction was stirred at 50° C. under nitrogen for 18 h. The reaction mixture was partitioned between diethyl ether (100 mL) and water (50 mL). The organic layer was washed with brine (50 mL) and dried over Na2SO4. Filtration, concentration under reduced pressure, followed by column chromatography (silica, eluent heptanes, 0-25% ethyl acetate) afforded 0.83 g of 2-(6-chloropyridine-3-sulfonyl)-2-methyl-propionic acid ethyl ester.

Workup

  1. customThe reaction mixture was partitioned between diethyl ether (100 mL) and water (50 mL)
  2. washThe organic layer was washed with brine (50 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationFiltration, concentration under reduced pressure

Sources & evidence

ORD record
ord-0df06ded69a84dbf8df62c5e1c9a3639
Source dataset
uspto-grants-2011_05
Patent number
US07935715B2

Reaction notes

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