Water → HCID 69022714, compound

HRID 1865112Notes

Reaction equation

HRID 1865112 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH3:21])[C:8](Br)=[C:9]([C:18]#[N:19])[C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][CH:12]=1)=[O:5])[CH3:2].[C-:22]#[N:23].[K+].O.C(Cl)Cl>CS(C)=O>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH3:21])[C:8]([C:22]#[N:23])=[C:9]([C:18]#[N:19])[C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][CH:12]=1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 9032Potassium CyanideHCID 69020222HCID 69020222, compound

Product 1

HCID 69022714HCID 69022714, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

Dissolve 5-bromo-3-(4-bromo-phenyl)-4-cyano-1-methyl-1H-pyrrole-2-carboxylic acid ethyl ester (205 mg, 0.500 mmol, prepared in example E-265) in DMSO (2.5 mL). Add potassium cyanide (325 mg, 5.0 mmol) to the mixture. Heat the mixture at 80° C. for 16 h. Add H2O (30 mL) and methylene chloride (30 mL) into the reaction mixture. Extract with H2O (5×30 mL). Combine the organic layers, dry over magnesium sulfate, filter, and concentrate under reduced pressure. Purify by flash chromatography (elution with 33% Et2O in hexanes) to provide the title compound (161 mg, 0.450 mmol, 90%). Mass spectrum (m/e): 375.0 (M+18). Rf=0.2 (50% Et2O in hexanes).

Workup

  1. extractionExtract with H2O (5×30 mL)
  2. dry with materialCombine the organic layers, dry over magnesium sulfate
  3. filtrationfilter
  4. concentrationconcentrate under reduced pressure
  5. customPurify by flash chromatography (elution with 33% Et2O in hexanes)

Sources & evidence

ORD record
ord-d707e26f577248f6a2e6bca647224c7b
Source dataset
uspto-grants-2009_12
Patent number
US07625932B2

Reaction notes

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