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

HRID 558173ノート

反応式

HRID 558173 の反応式
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

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-1f530c11d8ee4bd39eb35f4b5b3796c3
出典データセット
uspto-grants-2011_11
特許番号
US08063034B2

反応ノート

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