2,4-Difluoroaniline → HCID 45280130, compound

HRID 454861Notes

Reaction equation

HRID 454861 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([N:12]1[CH2:16][CH2:15][CH2:14][CH:13]1[CH3:17])=[N:7][N:6]=[CH:5]2.[F:18][C:19]1[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=1[NH2:26].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.C(=O)([O-])[O-].[K+].[K+]>C(O)(C)(C)C.CO.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]>[F:18][C:19]1[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=1[NH:26][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([N:12]1[CH2:16][CH2:15][CH2:14][CH:13]1[CH3:17])=[N:7][N:6]=[CH:5]2

Participants

8

Reactant 4

HCID 97092,4-DifluoroanilineHCID 11430Potassium CarbonateHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 46899466HCID 46899466, compound

Product 1

HCID 45280130HCID 45280130, compound

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 887MethanolSolventHCID 6386tert-ButanolSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 6-bromo-1-(2-methylpyrrolidin-1-yl)phthalazine (325 mg, 1.1 mmol), 2,4-difluorobenzenamine (287 mg, 2.2 mmol), Pd2(dba)3 (10.2 mg, 0.011 mmol), X-Phos (26.5 mg, 0.056 mmol), and potassium carbonate (384 mg, 2.8 mmol) in t-butanol (2.2 mL) was heated at 110° C. in an oil bath for 18 h. The mixture was cooled to RT, diluted with MeOH and filtered through a pad of Celite. The filtrate was concentrated. The resulting brown residue was purified by column chromatography (0-70% acetone in hexanes) to provide the title compound as a brown amorphous solid. MS (ESI, pos. ion) m/z: 341.2 (M+1).

Workup

  1. temperatureThe mixture was cooled to RT
  2. filtrationfiltered through a pad of Celite
  3. concentrationThe filtrate was concentrated
  4. customThe resulting brown residue was purified by column chromatography (0-70% acetone in hexanes)

Sources & evidence

ORD record
ord-ca376d91f01b4ef0ad7bfc4ce5b4b8e9
Source dataset
uspto-grants-2013_07
Patent number
US08497269B2

Reaction notes

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