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Potassium Carbonate → 5-((3,6-dibromo-9H-carbazol-9-yl)methyl)-3-(pyridin-2-yl)oxazolidin-2-one

HRID 62198
Notes
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Reaction equation

HRID 62198 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH2:16][CH:17]3[O:21][C:20](=[O:22])[NH:19][CH2:18]3)[C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][C:10]([Br:15])=[CH:9][CH:8]=3.I[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=1.C([O-])([O-])=O.[K+].[K+].C(Cl)Cl.CCOC(C)=O>CS(C)=O.CCOC(C)=O.[Cu]I>[Br:15][C:10]1[CH:9]=[CH:8][C:7]2[N:6]([CH2:16][CH:17]3[O:21][C:20](=[O:22])[N:19]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=4)[CH2:18]3)[C:5]3[C:13]([C:12]=2[CH:11]=1)=[CH:14][C:2]([Br:1])=[CH:3][CH:4]=3
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 2211262-IodopyridineHCID 21226138Dichloromethane ethylacetateHCID 580971985-((3,6-dibromo-9H-carbazol-9-yl)methyl)oxazolidin-2-one

Product 1

HCID 580971855-((3,6-dibromo-9H-carbazol-9-yl)methyl)-3-(pyridin-2-yl)oxazolidin-2-oneYield 79.4%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 5-((3,6-dibromo-9H-carbazol-9-yl)methyl)oxazolidin-2-one (0.0195 g, 0.0460 mmol), 2-iodopyridine (0.0209 g, 0.102 mmol), CuI (0.0009 g, 0.00460 mmol), and K2CO3 (0.0058 g, 0.0418 mmol) in 0.5 mL of DMSO was sealed tightly in a vial and heated at 130° C. for 12 hours. The reaction mixture was cooled and diluted with 20 mL EtOAc and washed with water 5×10 mL. The organic layer was dried over anhydrous Na2SO4 and evaporated to afford the crude product, which was subjected to silica gel chromatography using CH2Cl2/EtOAc as elute to afford 0.0183 g white solid as product, yield 79.4%.

Workup

  1. customwas sealed tightly in a vial and
  2. temperatureThe reaction mixture was cooled
  3. washwashed with water 5×10 mL
  4. dry with materialThe organic layer was dried over anhydrous Na2SO4
  5. customevaporated
  6. customto afford the crude product, which
  7. washas elute

Sources & evidence

ORD record
ord-144dda4aedab44798bc9ce08eb592cbf
Source dataset
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09446042B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes