Pyridine → HCID 11404180, compound

HRID 1794588Notes

Reaction equation

HRID 1794588 reaction equation
Br[C:2]1[N:6]([NH:7][C:8](=[O:18])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:15][CH2:16][CH3:17])[C:5]([CH2:19][CH2:20][CH3:21])=[N:4][C:3]=1[CH3:22].[Cu][C:24]#[N:25].N1C=CC=CC=1.[I-].[K+]>C(OCC)(=O)C>[C:24]([C:2]1[N:6]([NH:7][C:8](=[O:18])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:15][CH2:16][CH3:17])[C:5]([CH2:19][CH2:20][CH3:21])=[N:4][C:3]=1[CH3:22])#[N:25]

Participants

6

Reactant 4

HCID 1049PyridineHCID 4875Potassium IodideHCID 22222222HCID 22222222, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 11404180HCID 11404180, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

N-(5-Bromo-4-methyl-2-propylimidazol-1-yl)-2-ethoxybenzamide from Example 2a (0.5 g, 1.2 mmol) and copper(I) cyanide (0.3 g, 3.5 mmol) are introduced into 12.5 ml of pyridine and heated at 100° C. for 6 hours. Potassium iodide (23 mg, 0.56 mmol) is added to the mixture, which is then stirred for a further 6 hours at 100° C. The reaction mixture is cooled to room temperature and, after addition of 50 ml of ethyl acetate, washed with dilute alkaline H2O2 solution. The aqueous phase is re-extracted with ethyl acetate, and the combined ethyl acetate phase is concentrated, finally azeotroped with toluene and again concentrated.

Workup

  1. temperatureThe reaction mixture is cooled to room temperature
  2. washwashed
  3. additionwith dilute alkaline H2O2 solution
  4. extractionThe aqueous phase is re-extracted with ethyl acetate
  5. concentrationthe combined ethyl acetate phase is concentrated
  6. customfinally azeotroped with toluene
  7. concentrationagain concentrated

Sources & evidence

ORD record
ord-21204130c59a443198b5c1c02dd1113e
Source dataset
uspto-grants-2006_04
Patent number
US07022847B2

Reaction notes

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