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Cesium carbonate → 6-Cyclobutylsulfanyl-pyridine-2-carboxylic acid ethyl ester

HRID 62883
Notes
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Reaction equation

HRID 62883 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([SH:12])[N:7]=1)=[O:5])[CH3:2].C([O-])([O-])=O.[Cs+].[Cs+].Br[CH:20]1[CH2:23][CH2:22][CH2:21]1>CC#N>[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([S:12][CH:20]2[CH2:23][CH2:22][CH2:21]2)[N:7]=1)=[O:5])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 78110BromocyclobutaneHCID 178468955HCID 178468955, compound

Product 1

HCID 901182766-Cyclobutylsulfanyl-pyridine-2-carboxylic acid ethyl esterYield 93%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

After 6-mercapto-pyridine-2-carboxylic acid ethyl ester (0.40 g, 2.18 mmol) was dissolved in CH3CN (9 mL), Cs2CO3(2.667 g, 6.54 mmol) and bromo cyclobutane (0.385 mL, 3.27 mmol) were added thereto, and the mixture was stirred at 50° C. for 18 hours. After the termination of the reaction, the reactant was filtered, concentrated under reduced pressure, and purified by column chromatography (eluent, EtOAc/Hex=1/5) to obtain the title compound (0.481 g, 92%).

Workup

  1. customAfter the termination of the reaction
  2. filtrationthe reactant was filtered
  3. concentrationconcentrated under reduced pressure
  4. custompurified by column chromatography (eluent, EtOAc/Hex=1/5)

Sources & evidence

ORD record
ord-4a4cf27f8d9946788a2fdf48713ee108
Source dataset
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09447044B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes