1,2-Dimethoxyethane → 6-Chloro-1-(4-fluoro-2-methylphenyl)phthalazine

HRID 454866

Reaction equation

HRID 454866 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([Cl:12])=[CH:9][CH:10]=2)[CH:5]=[N:4][N:3]=1.[F:13][C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[C:16]([CH3:23])[CH:15]=1.C(=O)([O-])[O-].[Na+].[Na+].COCCOC>CO.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CCO>[Cl:12][C:8]1[CH:7]=[C:6]2[C:11](=[CH:10][CH:9]=1)[C:2]([C:17]1[CH:18]=[CH:19][C:14]([F:13])=[CH:15][C:16]=1[CH3:23])=[N:3][N:4]=[CH:5]2

Participants

8

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 2734665(4-Fluoro-2-methylphenyl)boronic acidHCID 143223331,6-Dichlorophthalazine

Product 1

HCID 667396776-Chloro-1-(4-fluoro-2-methylphenyl)phthalazine

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 1,6-dichlorophthalazine (5.39 g, 27.1 mmol), 4-fluoro-2-methylphenylboronic acid (5.00 g, 32.5 mmol), trans-dichlorobis(triphenylphosphine)palladium (II) (0.950 g, 1.35 mmol), and sodium carbonate (8.61 g, 81.2 mmol) in a 2:1 mixture of DME and EtOH (40 mL) was heated at 80° C. in an oil bath for 18 h. The mixture was cooled to room temperature, diluted with MeOH and filtered through a pad of Celite. The filtrate was concentrated over silica gel and purified using column chromatography (0-25% EtOAc in hexanes) to provide the title compound as a yellow crystalline solid. MS (ESI, pos. ion) m/z: 272.8 (M+1).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationfiltered through a pad of Celite
  3. concentrationThe filtrate was concentrated over silica gel
  4. custompurified

Sources & evidence

ORD record
ord-e58d42084b4e4f40a7c92999a1b40f21
Source dataset
uspto-grants-2013_07
Patent number
US08497269B2

Linked notes

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