Dimethylformamide → HCID 15063396, compound

HRID 475475Notes

Reaction equation

HRID 475475 reaction equation
CN(C=O)C.[NH:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[C:7]1/[CH:15]=[CH:16]/[C:17]([O:19][CH2:20][CH3:21])=[O:18].Br[CH2:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25].C([O-])([O-])=O.[Cs+].[Cs+]>CC(C)=O>[C:27]([O:26][C:24](=[O:25])[CH2:23][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[C:7]1/[CH:15]=[CH:16]/[C:17]([O:19][CH2:20][CH3:21])=[O:18])([CH3:30])([CH3:29])[CH3:28]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 79177tert-Butyl bromoacetateHCID 15063395HCID 15063395, compound

Product 1

HCID 15063396HCID 15063396, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
60 °C

Procedure

To a 0.1 M DMF solution of ethyl (2E)-3-(1H-indol-2-yl) acrylate from Step 2 was added 1.4 equiv. of BrCH2CO2-t-Bu and 2.1 equiv. of Cs2CO3. The reaction mixture was stirred at 60° C. for 24 h, and was then diluted with an equal volume of acetone and filtered. The filtrate was concentrated and the residue was purified by silica gel chromatography eluted with EtOAc/Hex (1:2) to give the title compound (98%) as a syrup.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated
  3. customthe residue was purified by silica gel chromatography
  4. washeluted with EtOAc/Hex (1:2)

Sources & evidence

ORD record
ord-ff28a2295e22468a80398790bc2d8ce2
Source dataset
uspto-grants-2014_01
Patent number
US08637541B2

Reaction notes

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