Toluene → 2-([1,1'-Biphenyl]-3-yl)-4,5-dimethylpyridine

HRID 2400236ノート

反応式

HRID 2400236 の反応式
[C:1]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:12]=[C:11]([CH3:13])[C:10](Br)=[CH:9][N:8]=2)[CH:2]=1.[CH3:21]B1OB(C)OB(C)O1.O.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2CCCCC2)C2C=C(C3C(OC)=CC=CC=3OC)C=CC=2)CCCCC1.O>[C:1]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:12]=[C:11]([CH3:13])[C:10]([CH3:21])=[CH:9][N:8]=2)[CH:2]=1

参加物

8

反応物 4

HCID 1140TolueneHCID 574072TrimethylboroxineHCID 22031701Potassium phosphate, tribasic, monohydrateHCID 710081052-([1,1'-Biphenyl]-3-yl)-5-bromo-4-methylpyridine

生成物 1

HCID 592948462-([1,1'-Biphenyl]-3-yl)-4,5-dimethylpyridine収率 87%

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 58401078Dicyclohexyl(2',6'-dimethoxybiphenyl-3-yl)phosphine触媒HCID 962Water溶媒

実験手順

2-([1,1′-Biphenyl]-3-yl)-5-bromo-4-methylpyridine 11.5 g (35.5 mmol), 2,4,6-trimethyl-1,3,5,2,4,6-trioxatriborinane (5.57 g, 44.3 mmol), dicyclohexyl(2′,6′-dimethoxy-[1,1′-biphenyl]-3-yl)phosphine (1.2 g, 2.84 mmol), Pd2dba3 (0.650 g, 0.709 mmol) and potassium phosphate tribasic monohydrate, 250 mL toluene and 25 mL of water were placed in flask under nitrogen. The reaction mixture was degassed with nitrogen for 20 minutes and heated to reflux for 24 h. After cooling, the organic layer was separated and the aqueous layer extracted 3×50 mL with dichloromethane, dried over sodium sulfate and evaporated. The crude product was chromatographed on silica gel with 5% dichloromethane in hexane to give 8.0 g (87%) of the product. The product was confirmed by NMR and GC/MS.

後処理

  1. customThe reaction mixture was degassed with nitrogen for 20 minutes
  2. temperatureheated
  3. temperatureto reflux for 24 h
  4. temperatureAfter cooling
  5. customthe organic layer was separated
  6. extractionthe aqueous layer extracted 3×50 mL with dichloromethane
  7. dry with materialdried over sodium sulfate
  8. customevaporated
  9. customThe crude product was chromatographed on silica gel with 5% dichloromethane in hexane

出典と根拠

ORDレコード
ord-159c40f7b7d946e198d822c08393aa61
出典データセット
uspto-grants-2014_08
特許番号
US08795850B2

反応ノート

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