(2-Methylpropyl)boronic acid → 8-Isobutyl-2,4-dimethyl-5,6-dihydrobenzo[c]acridine

HRID 716592

反応式

HRID 716592 の反応式
Cl[C:2]1[C:15]2[C:6](=[N:7][C:8]3[C:9]4[CH:19]=[C:18]([CH3:20])[CH:17]=[C:16]([CH3:21])[C:10]=4[CH2:11][CH2:12][C:13]=3[CH:14]=2)[CH:5]=[CH:4][CH:3]=1.[CH2:22](B(O)O)[CH:23]([CH3:25])[CH3:24]>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=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1>[CH2:22]([C:2]1[C:15]2[C:6](=[N:7][C:8]3[C:9]4[CH:19]=[C:18]([CH3:20])[CH:17]=[C:16]([CH3:21])[C:10]=4[CH2:11][CH2:12][C:13]=3[CH:14]=2)[CH:5]=[CH:4][CH:3]=1)[CH:23]([CH3:25])[CH3:24]

参加物

6

反応物 2

HCID 2734395(2-Methylpropyl)boronic acidHCID 712451148-Chloro-2,4-dimethyl-5,6-dihydrobenzo[c]acridine

生成物 1

HCID 712450678-Isobutyl-2,4-dimethyl-5,6-dihydrobenzo[c]acridine収率 99.6%

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl触媒HCID 1140Toluene溶媒

実験手順

8-chloro-2,4-dimethyl-5,6-dihydrobenzo[c]acridine (15.0 g, 51.1 mmol), isobutylboronic acid (7.8 g, 77 mmol), dicyclohexyl(2′,6′-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine (1.6 g, 4.08 mmol) potassium phosphate monohydrate (41.2 g, 179 mmol) were mixed in 300 mL of toluene. The system was degassed for 20 minutes. Pd2(dba)3 (0.93 g, 1.02 mmol) was then added and the system was refluxed overnight. After cooling to room temperature, the reaction mixture was filtered through a Celite® plug and eluted with 30% ethyl acetate in toluene. ˜19.5 crude liquid was obtained. The crude product was recrystallized from 5% acetone in hexane to obtain ˜14.9 g pure product (99.6%) which was confirmed by GC-MS.

後処理

  1. customThe system was degassed for 20 minutes
  2. temperaturethe system was refluxed overnight
  3. filtrationthe reaction mixture was filtered through a Celite® plug
  4. washeluted with 30% ethyl acetate in toluene
  5. custom˜19.5 crude liquid was obtained
  6. customThe crude product was recrystallized from 5% acetone in hexane

出典と根拠

ORDレコード
ord-0a2f15c120b34d139e1f4897172644b0
出典データセット
uspto-grants-2015_11
特許番号
US09190621B2

関連ノート

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