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

HRID 716592Notes

Reaction equation

HRID 716592 reaction equation
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]

Participants

6

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylCatalystHCID 1140TolueneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-0a2f15c120b34d139e1f4897172644b0
Source dataset
uspto-grants-2015_11
Patent number
US09190621B2

Reaction notes

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