HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Cesium carbonate → 5-(3-Cyano-4-phenylpyrrole-1-yl)-2-methoxymethoxy-benzoic acid ethyl ester

HRID 570847
Notes
Print preview

Reaction equation

HRID 570847 reaction equation
[C:1]1([C:7]2[C:8]([C:12]#[N:13])=[CH:9][NH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:14]([O:16][C:17](=[O:29])[C:18]1[CH:23]=[C:22](Br)[CH:21]=[CH:20][C:19]=1[O:25][CH2:26][O:27][CH3:28])[CH3:15].C(=O)([O-])[O-].[Cs+].[Cs+]>[Cu](I)I.CS(C)=O>[CH2:14]([O:16][C:17](=[O:29])[C:18]1[CH:23]=[C:22]([N:10]2[CH:11]=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[C:8]([C:12]#[N:13])=[CH:9]2)[CH:21]=[CH:20][C:19]=1[O:25][CH2:26][O:27][CH3:28])[CH3:15]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 37214604-Phenyl-1H-pyrrole-3-carbonitrileHCID 594778785-Bromo-2-methoxymethoxy-benzoic acid ethyl ester

Product 1

HCID 594776895-(3-Cyano-4-phenylpyrrole-1-yl)-2-methoxymethoxy-benzoic acid ethyl esterYield 60.3%

Reagents, catalysts & solvents 2

HCID 83717Copper iodide
Catalyst
HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 4-phenyl-1H-pyrrole-3-carbonitrile (0.2 g), 5-bromo-2-methoxymethoxy-benzoic acid ethyl ester (0.36 g), copper iodide (0.023 g), N,N-dimethylgrycine (0.025 g), cesium carbonate (0.39 g) and dimethylsulfoxide (3 mL) was stirred at 75° C. for 12 hours. After cooling to ambient temperature, the insoluble material was removed by filtration through Celite pad, and this filtrate was concentrated. This obtained residue was purified by column chromatography on silica gel (eluent: ethyl acetate/n-hexane=10/90-66/34) to give the title compound (0.27 g).

Workup

  1. temperatureAfter cooling to ambient temperature
  2. customthe insoluble material was removed by filtration through Celite pad
  3. concentrationthis filtrate was concentrated
  4. customThis obtained residue was purified by column chromatography on silica gel (eluent: ethyl acetate/n-hexane=10/90-66/34)

Sources & evidence

ORD record
ord-f1c7bbccf296464e94ceb25e50dbcd39
Source dataset
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09023882B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes