2,4-Difluoroaniline → HCID 45280243, compound

HRID 454872Notes

Reaction equation

HRID 454872 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([O:12][CH:13]([CH3:18])[C:14]([F:17])([F:16])[F:15])=[N:7][N:6]=[CH:5]2.CC(C)([O-])C.[Na+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2)CCCCC1.[F:50][C:51]1[CH:57]=[C:56]([F:58])[CH:55]=[CH:54][C:52]=1[NH2:53]>C1(C)C=CC=CC=1.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:50][C:51]1[CH:57]=[C:56]([F:58])[CH:55]=[CH:54][C:52]=1[NH:53][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([O:12][CH:13]([CH3:18])[C:14]([F:17])([F:16])[F:15])=[N:7][N:6]=[CH:5]2

Participants

8

Reactant 4

HCID 97092,4-DifluoroanilineHCID 27342162-(Dicyclohexylphosphino)biphenylHCID 23676156Sodium t-butoxideHCID 25129833HCID 25129833, compound

Product 1

HCID 45280243HCID 45280243, compound

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 887MethanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 6-bromo-1-(1,1,1-trifluoropropan-2-yloxy)phthalazine (0.130 g, 0.40 mmol), sodium t-butoxide (0.056 g, 0.58 mmol), tris(dibenzylideneacetone)dipalladium (0) (0.016 g, 0.017 mmol), 2-(dicyclohexylphosphino)biphenyl (0.022 g, 0.063 mmol) and 2,4-difluoroaniline (0.060 ml, 0.60 mmol) in 1.5 mL of toluene was heated at 140° C. for 15 min in the microwave (Initiator by Biotage). The mixture was diluted with MeOH, evaporated onto silica gel and purified by flash chromatography (ISCO 12 g, eluting with 15-75% EtOAc in hexanes) to give the title compound as a light-yellow amorphous solid. MS (ESI, pos. ion) m/z: M+1=370.1

Workup

  1. customevaporated onto silica gel
  2. custompurified by flash chromatography (ISCO 12 g, eluting with 15-75% EtOAc in hexanes)

Sources & evidence

ORD record
ord-df87284790244c6d8429c915e787f30d
Source dataset
uspto-grants-2013_07
Patent number
US08497269B2

Reaction notes

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