Toluene → HCID 60166989, compound

HRID 473508Notes

Reaction equation

HRID 473508 reaction equation
Cl[C:2]1[CH:27]=[CH:26][C:5]2[C:6](=[O:25])[C:7]3[CH:14]=[C:13]([O:15][CH2:16][CH2:17][C@@H:18]4[CH2:22][O:21][C:20]([CH3:24])([CH3:23])[O:19]4)[CH:12]=[CH:11][C:8]=3[CH2:9][CH2:10][C:4]=2[CH:3]=1.[F:28][C:29]1[CH:35]=[C:34]([F:36])[CH:33]=[CH:32][C:30]=1[NH2:31].C1(C)C=CC=CC=1>CC([O-])=O.CC([O-])=O.[Pd+2].C(O)(C)(C)C>[F:28][C:29]1[CH:35]=[C:34]([F:36])[CH:33]=[CH:32][C:30]=1[NH:31][C:2]1[CH:27]=[CH:26][C:5]2[C:6](=[O:25])[C:7]3[CH:14]=[C:13]([O:15][CH2:16][CH2:17][C@@H:18]4[CH2:22][O:21][C:20]([CH3:24])([CH3:23])[O:19]4)[CH:12]=[CH:11][C:8]=3[CH2:9][CH2:10][C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 1140TolueneHCID 97092,4-DifluoroanilineHCID 67498284HCID 67498284, compound

Product 1

HCID 60166989HCID 60166989, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6386tert-ButanolSolvent

Procedure

In accordance with general method AA, 0.70 g (1.8 mmol) of 2-chloro-7-(2((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethoxy]-10,11-dihydrodibenzo[a,d]-cyclohepten-5-one (360, 0.25 g (1.9 mmol) of 2,4-difluoroaniline, 0.05 g (0.22 mmol) of Pd(OAc)2, 0.10 g (0.21 mmol) of 2-(dicyclohexylphosphino)-2′-, 4′-,6′-triisopropyl-biphenyl, 0.60 g (6.2 mmol) of Na—O-tert-butylate, 5 ml of toluene and 1 ml of tert-BuOH are used. Reaction time: 1 h. Purification is carried out via flash chromatography (SiO2, hexane/ethyl acetate 7+3). Yield: 45%;

Workup

  1. customReaction time
  2. custom1 h
  3. customPurification

Sources & evidence

ORD record
ord-213c15f7ef8346a3923c7993408700ec
Source dataset
uspto-grants-2014_01
Patent number
US08633312B2

Reaction notes

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