Water → HCID 69083608, compound

HRID 1023463Notes

Reaction equation

HRID 1023463 reaction equation
Br[C:2]1[CH:7]=[C:6]([C:8]2[O:12][CH:11]=[N:10][C:9]=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+:21].O>O1CCOCC1.[Cu-]=O>[F:19][C:16]1[CH:17]=[CH:18][C:13]([C:9]2[N:10]=[CH:11][O:12][C:8]=2[C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH2:21])[CH:7]=2)=[CH:14][CH:15]=1

Participants

6

Reactant 3

HCID 962WaterHCID 14923Ammonium HydroxideHCID 86673614HCID 86673614, compound

Product 1

HCID 69083608HCID 69083608, compound

Reagents, catalysts & solvents 2

HCID 178419072HCID 178419072, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
150 °C

Procedure

2-Bromo-4-[4-(4-fluoro-phenyl)-oxazol-5-yl]-pyridine (700 mg, 2.19 mmol), 28% aqueous ammonium hydroxide solution (14 mL) and Copper (I) oxide (314 mg, 2.19 mmol) are mixed in 1,4-dioxane (14 mL) in a microwave reaction tube. The tube is sealed and heated at 150° C. for 25 min in a microwave reactor. Then water (80 mL) is added and the mixture is extracted with EtOAc (3×50 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 320 mg of desired product.

Workup

  1. customThe tube is sealed
  2. extractionthe mixture is extracted with EtOAc (3×50 ml)
  3. concentrationconcentrated
  4. customto give the crude product
  5. customPurification by silica flash column chromatography

Sources & evidence

ORD record
ord-7487d83232a949bb8190db9f771fb467
Source dataset
uspto-grants-2014_05
Patent number
US08722709B2

Reaction notes

Loading…