Potassium Carbonate → HCID 44430595, compound

HRID 646186Notes

Reaction equation

HRID 646186 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](/[C:8](=[CH:11]/[C:12]2[NH:13][CH:14]=[CH:15][CH:16]=2)/[C:9]#[N:10])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH3:23][C:24]([CH3:28])=[CH:25][CH2:26]Br>CC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5](/[C:8](=[CH:11]/[C:12]2[N:13]([CH2:26][CH:25]=[C:24]([CH3:28])[CH3:23])[CH:14]=[CH:15][CH:16]=2)/[C:9]#[N:10])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 700922-Butene, 1-bromo-3-methyl-HCID 6074183HCID 6074183, compound

Product 1

HCID 44430595HCID 44430595, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of (Z)-2-(4-Chloro-phenyl)-3-(1H-pyrrol-2-yl)acrylonitrile being Compound 2 in Table 8 (200 mg, 0.875 mmol) in dry acetone (35 ml) was treated with K2CO3 (121 mg) followed by dimethylallyl bromide (111 μl, 0.962 mmol, 1.1 equivalents). The mixture was heated to a gentle reflux for 20 h. The reaction was cooled to room temperature and filtered. The filtrate was chromatographed on silica gel using ethylacetate/petroleum spirits (1:1) as eluant to afford the title compound as a yellow oil (85 mg). This is Compound 80 in Table 8.

Workup

  1. temperatureThe mixture was heated to
  2. temperaturea gentle reflux for 20 h
  3. filtrationfiltered
  4. customThe filtrate was chromatographed on silica gel

Sources & evidence

ORD record
ord-45f5280980ca401ab50a5850f8c11181
Source dataset
uspto-grants-2010_04
Patent number
US07705038B2

Reaction notes

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