2-Aminobiphenyl → N-[1,1'-Biphenyl]-2-YL-4-dibenzofuranamine

HRID 929274

反応式

HRID 929274 の反応式
C1(P(C2CCCCC2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14]2[C:19](OC)=[CH:18][CH:17]=[CH:16][C:15]=2[O:22]C)CCCCC1.[C:30]1([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:31]([NH2:36])=[CH:32][CH:33]=[CH:34][CH:35]=1.IC1C2OC3C=CC=CC=3C=2C=CC=1.CC(C)([O-])C.[Na+]>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]>[C:30]1([C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[NH:36][C:16]1[C:15]2[O:22][C:10]3[CH:11]=[CH:12][CH:13]=[CH:8][C:9]=3[C:14]=2[CH:19]=[CH:18][CH:17]=1

参加物

6

反応物 4

HCID 70152-AminobiphenylHCID 4582574-IododibenzofuranHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 23676156Sodium t-butoxide

生成物 1

HCID 68904161N-[1,1'-Biphenyl]-2-YL-4-dibenzofuranamine収率 837.7%

試薬・触媒・溶媒 1

HCID 9811564Bis(dibenzylideneacetone)palladium触媒

実験手順

Toluene (250 mL) was bubbled with nitrogen for 15 min, followed by addition of 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (1.7 g, 4.2 mmol), and Pd2(dba)3 (1.0 g, 1.1 mmol). The mixture was bubbled with nitrogen for 15 min, then [1,1′-biphenyl]-2-amine (3.4 g, 20.0 mmol), 4-iododibenzo[b,d]furan (10.3 g, 35.0 mmol), and sodium tert-butoxide (6.7 g, 70.0 mmol) were added. The mixture was bubbled with nitrogen for 15 min and refluxed for 24 h. After cooling, the reaction mixture was filtered through a silica pad and washed with DCM. The solvent was removed in vacuo and the residue was purified by flash chromatography using 25% DCM/hexane (containing 0.75% triethylamine) to yield N-([1,1′-biphenyl]-2-yl)dibenzo[b,d]furan-4-amine (11.8 g, 98% yield) as a colorless oil.

後処理

  1. customToluene (250 mL) was bubbled with nitrogen for 15 min
  2. customThe mixture was bubbled with nitrogen for 15 min
  3. customThe mixture was bubbled with nitrogen for 15 min
  4. temperaturerefluxed for 24 h
  5. temperatureAfter cooling
  6. filtrationthe reaction mixture was filtered through a silica pad
  7. washwashed with DCM
  8. customThe solvent was removed in vacuo
  9. customthe residue was purified by flash chromatography

出典と根拠

ORDレコード
ord-a43bcae1d0cb4982a89c74011ebd7937
出典データセット
uspto-grants-2016_03
特許番号
US09293712B2

関連ノート

読み込み中…