7-Bromo-5-methoxy-2-(4-methoxyphenyl)-1,3-benzoxazole → HCID 22144541, compound

HRID 1824788Notes

Reaction equation

HRID 1824788 reaction equation
Br[C:2]1[C:10]2[O:9][C:8]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)=[N:7][C:6]=2[CH:5]=[C:4]([O:19][CH3:20])[CH:3]=1.[C:21]([Cu])#[N:22]>CN(C=O)C.C(OCC)(=O)C>[CH3:20][O:19][C:4]1[CH:3]=[C:2]([C:21]#[N:22])[C:10]2[O:9][C:8]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)=[N:7][C:6]=2[CH:5]=1

Participants

5

Reactant 2

HCID 121489697-Bromo-5-methoxy-2-(4-methoxyphenyl)-1,3-benzoxazoleHCID 178418546HCID 178418546, compound

Product 1

HCID 22144541HCID 22144541, compoundYield 50.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

To 7-bromo-5-methoxy-2-(4-methoxy-phenyl)-benzooxazole (200 mg) in DMF (5 mL) was added CuCN (80 mg). The mixture was placed in an oil bath and heated to 150° C. for 3 h. The mixture was cooled to room temperature and diluted with ethyl acetate and washed with 1N HCl, brine (3×), dried (Na2SO4), and concentrated. Flash chromatography on silica gel eluting with 20% ethyl acetate-hexane afforded 85 mg (50%) of the title compound as a solid. MS: 281 (MH+), HPLC tR: 2.71 min.

Workup

  1. customThe mixture was placed in an oil bath
  2. temperatureThe mixture was cooled to room temperature
  3. washwashed with 1N HCl, brine (3×)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-655828843d404bc0a0387112ddefbeef
Source dataset
uspto-grants-2006_05
Patent number
US07045539B2

Reaction notes

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