Dimethylformamide → 3-Methoxycarbonylvinylcarbazole

HRID 1008660Notes

Reaction equation

HRID 1008660 reaction equation
CN(C=O)C.I[C:7]1[CH:8]=[CH:9][C:10]2[NH:11][C:12]3[C:17]([C:18]=2[CH:19]=1)=[CH:16][CH:15]=[CH:14][CH:13]=3.C(N(CCCC)CCCC)CCC.[C:33]([O:37][CH3:38])(=[O:36])[CH:34]=[CH2:35]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH3:38][O:37][C:33]([CH:34]=[CH:35][C:7]1[CH:8]=[CH:9][C:10]2[NH:11][C:12]3[C:17]([C:18]=2[CH:19]=1)=[CH:16][CH:15]=[CH:14][CH:13]=3)=[O:36]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 7294Methyl AcrylateHCID 7622TributylamineHCID 36780693-iodo-9H-carbazole2×

Product 1

HCID 668960893-MethoxycarbonylvinylcarbazoleYield 62%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent

Procedure

To a DMF solution (0.25 mL) of palladium acetate (38.0 mg, 0.17 μmol), compound 1 (0.50 g, 1.71 mmol), tributylamine (0.41 μL, 1.71 mmol), methyl acrylate (0.38 L, 4.27 mmol), and H2O (1.0 mL) were sequentially added. The reaction solution was allowed to react at 160° C. for 10 minutes using microwaves, and the reaction was traced by TLC. Thereby, the loss of compound 1 was confirmed. The palladium powder was removed by Kiriyama filtration, and then the reaction solution was purified by column chromatography (HexH:AcOEt=3:1), and thus compound 7 (0.26 g, 62%) was obtained as a white powder.

Workup

  1. customto react at 160° C. for 10 minutes
  2. customThe palladium powder was removed by Kiriyama filtration
  3. customthe reaction solution was purified by column chromatography (HexH:AcOEt=3:1)

Sources & evidence

ORD record
ord-4f219fe901ea47398e1918c73013565a
Source dataset
uspto-grants-2011_07
Patent number
US07972792B2

Reaction notes

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