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(2-Methylpropyl)boronic acid → 2-(3,5-Dimethylphenyl)-6,7-diisobutylquinoline

HRID 1505744
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HRID 1505744 반응식
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1Cl)[N:8]=[C:7]([C:13]1[CH:18]=[C:17]([CH3:19])[CH:16]=[C:15]([CH3:20])[CH:14]=1)[CH:6]=[CH:5]2.[CH2:21](B(O)O)[CH:22]([CH3:24])[CH3:23].C1(P(C2CCCCC2)[C:35]2C=CC=[CH:37][C:36]=2[C:41]2C(OC)=CC=CC=2OC)CCCCC1.O.P([O-])([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].O>[CH3:20][C:15]1[CH:14]=[C:13]([C:7]2[CH:6]=[CH:5][C:4]3[C:9](=[CH:10][C:11]([CH2:35][CH:36]([CH3:41])[CH3:37])=[C:2]([CH2:21][CH:22]([CH3:24])[CH3:23])[CH:3]=3)[N:8]=2)[CH:18]=[C:17]([CH3:19])[CH:16]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 2734395(2-Methylpropyl)boronic acidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 22031701Potassium phosphate, tribasic, monohydrateHCID 866849816-Bromo-7-chloro-2-(3,5-dimethylphenyl)quinoline

생성물 1

HCID 866849802-(3,5-Dimethylphenyl)-6,7-diisobutylquinoline수율 413.6%

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 962Water용매HCID 1140Toluene용매

실험 절차

6-Bromo-7-chloro-2-(3,5-dimethylphenyl)quinoline (5.2 g, 15.0 mmol), isobutylboronic acid (6.12 g, 60.0 mmol), dicyclohexyl(2′,6′-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine (0.99 g, 2.4 mmol), Pd2(dba)3 (0.549 g, 0.60 mmol), potassium phosphate monohydrate (34.5 g, 150 mmol) and 2 mL of water were mixed in 240 mL of toluene. The system was degassed with nitrogen for 20 minutes and refluxed overnight. After cooling to room temperature, the reaction mixture was filtered through a Celite® plug and eluted with dichloromethane. The product was purified by column chromatography, eluting with 2:1 (v/v) hexanes:DCM, to give 2-(3,5-dimethylphenyl)-6,7-diisobutylquinoline (3.43 g, 66%).

후처리

  1. customThe system was degassed with nitrogen for 20 minutes
  2. temperaturerefluxed overnight
  3. filtrationthe reaction mixture was filtered through a Celite® plug
  4. washeluted with dichloromethane
  5. customThe product was purified by column chromatography
  6. washeluting with 2:1 (v/v) hexanes

출처 및 근거

ORD 기록
ord-39b7a24feb88495ab292b3423e8c322c
출처 데이터셋
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09217004B2

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