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

HRID 1505744
ノート
印刷プレビュー

反応式

HRID 1505744 の反応式
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
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 962Water溶媒HCID 1140Toluene溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-39b7a24feb88495ab292b3423e8c322c
出典データセット
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09217004B2

反応ノート

読み込み中…

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