Diisopropylethylamine → HCID 44481474, compound

HRID 452788

Reaction equation

HRID 452788 reaction equation
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[C:17]3[CH:18]=[C:19]([C:22]4[O:23][C:24]([CH3:27])=[N:25][N:26]=4)[CH:20]=[CH:21][C:16]=3[O:15][CH:14]=2)=[CH:9][CH:8]=1)(=O)=O.[P:30]([O-:35])([O:33][CH3:34])[O:31][CH3:32].C(N(CC)C(C)C)(C)C>C1(C)C=CC=CC=1.C(OCC)(=O)C.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>[CH3:32][O:31][P:30]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[C:17]3[CH:18]=[C:19]([C:22]4[O:23][C:24]([CH3:27])=[N:25][N:26]=4)[CH:20]=[CH:21][C:16]=3[O:15][CH:14]=2)=[CH:9][CH:8]=1)(=[O:35])[O:33][CH3:34]

Participants

7

Reactant 3

HCID 81531DiisopropylethylamineHCID 21884954DimethylphosphiteHCID 866400464-[5-(5-Methyl-1,3,4-oxadiazol-2-yl)-1-benzofuran-3-yl]phenyl trifluoromethanesulfonate

Product 1

HCID 44481474HCID 44481474, compoundYield 55%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-[5-(5-methyl-1,3,4-oxadiazol-2-yl)-1-benzofuran-3-yl]phenyl trifluoromethanesulfonate (391 mg, 0.900 mmol), dimethyl phosphite (0.165 mL, 1.80 mmol), tetrakis(triphenylphosphine)palladium(0) (104 mg, 0.0900 mmol) and N,N-diisopropylethylamine (0.314 mL, 1.80 mmol) in toluene (5 mL) was stirred at 100° C. for 2 hr under an argon atmosphere. After cooling, the reaction mixture was diluted with ethyl acetate, washed with 1M hydrochloric acid and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (ethyl acetate) and recrystallized from hexane/ethyl acetate to give the title compound (190 mg, yield 55%) as colorless crystals.

Workup

  1. temperatureAfter cooling
  2. washwashed with 1M hydrochloric acid and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by basic silica gel column chromatography (ethyl acetate)
  6. customrecrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-c4cbe7b36a8346898501a35437bcc19e
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Linked notes

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