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

HRID 716592

반응식

HRID 716592 반응식
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]

참가 물질

6

반응물 2

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

생성물 1

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

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl촉매HCID 1140Toluene용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-0a2f15c120b34d139e1f4897172644b0
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09190621B2

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