Sodium Carbonate → HCID 67170289, compound

HRID 872840Notes

Reaction equation

HRID 872840 reaction equation
C1(S([CH:9]([C:20]2[O:21][C:22]([Br:25])=[CH:23][CH:24]=2)[CH2:10][NH:11][C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)=[O:13])=O)C=CC=CC=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1>[Br:25][C:22]1[O:21][C:20](/[CH:9]=[CH:10]/[NH:11][C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)=[O:13])=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 67168441HCID 67168441, compound

Product 1

HCID 67170289HCID 67170289, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The mixture of pyridine-2-carboxylic acid [2-benzenesulfinyl-2-(5-bromofuran-2-yl)ethyl]amide (0.11 g, 0.2623 mmol) and Na2CO3 (0.03 g, 0.2623 mmol) in toluene was refluxed in nitrogen atmosphere for 2 h. The toluene solution was washed with 1 M NaOH (25 ml), dried with Na2SO4 and evaporated. The crude product was purified by flash chromatography using heptane-EtOAc as a gradient eluent (90:10-80:20). The E isomer was used in the next step.

Workup

  1. temperaturewas refluxed in nitrogen atmosphere for 2 h
  2. washThe toluene solution was washed with 1 M NaOH (25 ml)
  3. dry with materialdried with Na2SO4
  4. customevaporated
  5. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-c626559bf0294de4ab25ffff1f8808e3
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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