Water → HCID 69093926, compound

HRID 1023461Notes

Reaction equation

HRID 1023461 reaction equation
Br[C:2]1[CH:7]=[C:6]([C:8]2[N:9]=[CH:10][N:11]([CH3:20])[C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[CH:5]=[CH:4][N:3]=1.[OH-].[NH4+:22].O>O1CCOCC1.[Cu-]=O>[F:19][C:16]1[CH:17]=[CH:18][C:13]([C:12]2[N:11]([CH3:20])[CH:10]=[N:9][C:8]=2[C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH2:22])[CH:7]=2)=[CH:14][CH:15]=1

Participants

6

Reactant 3

HCID 962WaterHCID 14923Ammonium HydroxideHCID 86673613HCID 86673613, compound

Product 1

HCID 69093926HCID 69093926, compound

Reagents, catalysts & solvents 2

HCID 178419072HCID 178419072, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

The crude 2-Bromo-4-[5-(4-fluoro-phenyl)-1-methyl-1H-imidazol-4-yl]-pyridine (196 mg), 28% aqueous ammonium hydroxide solution (2.0 mL) and copper (I) oxide (84 mg, 0.59 mmol) are mixed in 1,4-dioxane (3.0 mL) in a microwave reaction tube. The mixture is heated at 150° C. for 25 min in a microwave reactor before water (30 mL) is added. The resulting mixture is extracted with EtOAc (3×25 ml). The organic layers are combined and concentrated to give the crude product. Purification by silica flash column chromatography using MeOH in DCM (gradient from 0% to 10%) affords 72 mg of desired product.

Workup

  1. additionis added
  2. extractionThe resulting mixture is extracted with EtOAc (3×25 ml)
  3. concentrationconcentrated
  4. customto give the crude product
  5. customPurification by silica flash column chromatography

Sources & evidence

ORD record
ord-a4d3cd40875d441a88ef9ebcc6ff1f87
Source dataset
uspto-grants-2014_05
Patent number
US08722709B2

Reaction notes

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