Diisopropylethylamine → N-Phenyl-5-(2-(pyridin-4-yl)methylthiophenyl)-1,3,4-oxadiazol-2-amine

HRID 558173Notes

Reaction equation

HRID 558173 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[O:12][C:11]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[N:10][N:9]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C(N(C(C)C)CC)(C)C.Cl.[N:72]1[CH:77]=[CH:76][C:75]([CH2:78][SH:79])=[CH:74][CH:73]=1>C(OCC)(=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[C:14]1([NH:13][C:11]2[O:12][C:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[S:79][CH2:78][C:75]3[CH:76]=[CH:77][N:72]=[CH:73][CH:74]=3)=[N:9][N:10]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

8

Reactant 4

HCID 81531DiisopropylethylamineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 230938734-Pyridinemethanethiol hydrochlorideHCID 591525395-(2-bromophenyl)-N-phenyl-1,3,4-oxadiazol-2-amine

Product 1

HCID 24992355N-Phenyl-5-(2-(pyridin-4-yl)methylthiophenyl)-1,3,4-oxadiazol-2-amineYield 71.3%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A vessel containing 5-(2-bromophenyl)-N-phenyl-1,3,4-oxadiazol-2-amine (220 mg, 0.70 mmol; Reference Compound 7-(1)), tris(dibenzylideneacetone)dipalladium (33 mg, 0.035 mmol) and Xantphos (81 mg, 0.14 mmol) was replaced with nitrogen gas. To the vessel were added dioxane (5.0 mL), diisopropylethylamine (0.43 mL, 2.5 mmol) and 4-pyridinemethanethiol hydrochloride (210 mg, 1.3 mmol) successively at room temperature, and then the mixture was refluxed overnight. The reaction solution was cooled to room temperature and diluted with ethyl acetate (15 mL). The ethyl acetate solution was washed with a saturated brine solution (20 mL), dried over anhydrous sodium sulfate and concentrated under a reduced pressure. To the residue was added ethanol and a precipitated solid was filtered off and dried to give 180 mg (70%) of the titled compound as a pale brown solid.

Workup

  1. temperaturethe mixture was refluxed overnight
  2. washThe ethyl acetate solution was washed with a saturated brine solution (20 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under a reduced pressure
  5. additionTo the residue was added ethanol
  6. filtrationa precipitated solid was filtered off
  7. customdried

Sources & evidence

ORD record
ord-1f530c11d8ee4bd39eb35f4b5b3796c3
Source dataset
uspto-grants-2011_11
Patent number
US08063034B2

Reaction notes

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