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

HRID 1774093노트

반응식

HRID 1774093 반응식
[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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 58401078Dicyclohexyl(2',6'-dimethoxybiphenyl-3-yl)phosphine촉매HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-788cc326f9314efead3869fff521b9c6
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09257658B2

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