Dimethylformamide → 3-Methoxycarbonylvinylcarbazole

HRID 448515Notes

Reaction equation

HRID 448515 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) as well as tributylamine (0.41 μL, 1.71 mmol), methyl acrylate (0.38 L, 4.27 mmol) and H2O (1.0 mL) were added in this order. The reaction solution was allowed to react for 10 minutes at 160° C. using microwaves, and the reaction was traced by TLC to confirm the disappearance of compound (1). The palladium powder was removed by Kiriyama filtration, and then the residue was purified by column chromatography (HexH:AcOEt=3:1). Thus, compound (7) (0.26 g, 62%) was obtained as a white powder.

Workup

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

Sources & evidence

ORD record
ord-570aca7291c54e3395455cea8e0bcd9f
Source dataset
uspto-grants-2013_07
Patent number
US08481714B2

Reaction notes

Loading…