Ethyl Acetate → Benzoxazole, 5-nitro-2-(2-thienyl)-

HRID 1896768Notes

Reaction equation

HRID 1896768 reaction equation
Cl[C:2]1[O:3][C:4]2[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:5]=2[N:6]=1.C([Sn](CCCC)(CCCC)[C:19]1[S:20][CH:21]=[CH:22][CH:23]=1)CCC.C(OCC)(=O)C>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[N+:11]([C:8]1[CH:9]=[CH:10][C:4]2[O:3][C:2]([C:19]3[S:20][CH:21]=[CH:22][CH:23]=3)=[N:6][C:5]=2[CH:7]=1)([O-:13])=[O:12]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 27793732-(Tri-n-butylstannyl)thiopheneHCID 103527232-Chloro-5-nitrobenzo[d]oxazole

Product 1

HCID 11253621Benzoxazole, 5-nitro-2-(2-thienyl)-Yield 2%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-chloro-5-nitrobenzo[d]oxazole (404 mg, 2.04 mmol), 2-(tributylstannyl)-thiophene (648 μL, 2.04 mmol) and tetrakis(triphenylphosphine)palladium (0) (40.8 mg) in dioxane (12.2 mL) was heated at 100° C. for 16 h under nitrogen. Ethyl acetate was added, the organic layer was washed with water, dried over anhydrous MgSO4 and evaporated. The resulting solid was purified by column chromatography eluting with ethyl acetate/hexanes 10:90 v/v, and then purified by reverse phase HPLC to afford 3 mg (2%) of the title product (LCMS RT=6.95 min)

Workup

  1. washthe organic layer was washed with water
  2. dry with materialdried over anhydrous MgSO4
  3. customevaporated
  4. customThe resulting solid was purified by column chromatography
  5. washeluting with ethyl acetate/hexanes 10:90 v/v
  6. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-4dfa609c772d4eed8613ae6eb5efd024
Source dataset
uspto-grants-2013_08
Patent number
US08518980B2

Reaction notes

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