1,2-Dimethoxyethane → 1-Benzyl-5-(2,4-dimethylphenyl)-3-methylcinnolin-4(1H)-one

HRID 598159Notes

Reaction equation

HRID 598159 reaction equation
[CH2:1]([N:8]1[C:17]2[C:12](=[C:13](Cl)[CH:14]=[CH:15][CH:16]=2)[C:11](=[O:19])[C:10]([CH3:20])=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F-].[Cs+].C(COC)OC.[CH3:29][C:30]1[CH:35]=[C:34]([CH3:36])[CH:33]=[CH:32][C:31]=1B(O)O>C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([N:8]1[C:17]2[C:12](=[C:13]([C:31]3[CH:32]=[CH:33][C:34]([CH3:36])=[CH:35][C:30]=3[CH3:29])[CH:14]=[CH:15][CH:16]=2)[C:11](=[O:19])[C:10]([CH3:20])=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 25953Cesium fluorideHCID 4198739(2,4-Dimethylphenyl)boronic acidHCID 672671161-Benzyl-5-chloro-3-methylcinnolin-4(1H)-one

Product 1

HCID 589386481-Benzyl-5-(2,4-dimethylphenyl)-3-methylcinnolin-4(1H)-oneYield 71.9%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To 0.115 g (0.40 mmol) of 1-benzyl-5-chloro-3-methylcinnolin-4(1H)-one, 0.12 g (0.81 mmol) of cesium fluoride and 0.093 g (0.08 mmol) of tetrakis(triphenylphosphine)palladium(0) was added 4 mL of dimethoxyethane. The dark brown mixture was stirred at room temperature for 15 min. then 0.079 g (0.53 mmol) of 2,4-dimethylphenylboronic acid was added. This mixture was then heated to reflux for 5 h, cooled to room temperature, diluted with ethyl acetate and filtered through a plug of silica gel. The resulting filtrate was concentrated and the residue was purified by flash chromatography eluting with a 17% ethyl acetate/hexanes mixture to give 0.102 g (71%) of the title compound as a light yellow solid.

Workup

  1. temperatureThis mixture was then heated
  2. temperatureto reflux for 5 h
  3. temperaturecooled to room temperature
  4. filtrationfiltered through a plug of silica gel
  5. concentrationThe resulting filtrate was concentrated
  6. customthe residue was purified by flash chromatography
  7. washeluting with a 17% ethyl acetate/hexanes mixture

Sources & evidence

ORD record
ord-1baa510bb1a54f57af415743e0bca771
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Reaction notes

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