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2,4-Difluoroaniline → 5-(2,6-difluorophenyl)-2-[(2,4-difluorophenyl)amino]-6H-pyrido[1,2-b]pyridazin-6-one

HRID 1454968
Notes
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Reaction equation

HRID 1454968 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[CH:9][C:10](=[O:20])[C:11]=2[C:12]2[C:17]([F:18])=[CH:16][CH:15]=[CH:14][C:13]=2[F:19])[N:7]=1.[O-]CCCC.[Na+].[F:27][C:28]1[CH:34]=[C:33]([F:35])[CH:32]=[CH:31][C:29]=1[NH2:30]>C1(C)C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2]>[F:19][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]([F:18])[C:12]=1[C:11]1[C:10](=[O:20])[CH:9]=[CH:8][N:6]2[C:5]=1[CH:4]=[CH:3][C:2]([NH:30][C:29]1[CH:31]=[CH:32][C:33]([F:35])=[CH:34][C:28]=1[F:27])=[N:7]2
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 97092,4-DifluoroanilineHCID 23669364Sodium n-butylateHCID 575312262-chloro-5-(2,6-difluorophenyl)-6H-pyrido[1,2-b]pyridazin-6-one

Product 1

HCID 167499415-(2,6-difluorophenyl)-2-[(2,4-difluorophenyl)amino]-6H-pyrido[1,2-b]pyridazin-6-one

Reagents, catalysts & solvents 2

HCID 635956
Ferrocene-1,1'-bis-(diphenylphosphine)
Catalyst
HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-chloro-5-(2,6-difluorophenyl)-6H-pyrido[1,2-b]pyridazin-6-one (100 mg, 0.34 mmol) dissolved in toluene (1.5 mL) was added Pd(DBA) (3.1 mg, 0.0034 mmol), dppf (3.7 mg, 0.0068 mmol), sodium butoxide (23 mg, 0.238 mmol), and 2,4 difluoro aniline (43 mg, 0.34 mmol). The reaction was heated to 80° C. for 3 hours until complete by LCMS analysis. The reaction was passed through celite, condensed to an oil and purified via silica gel chromatography (EtOAc/CH2Cl2, MeOH) to yield the title compound.

Workup

  1. customThe reaction was passed through celite, condensed to an oil
  2. custompurified via silica gel chromatography (EtOAc/CH2Cl2, MeOH)

Sources & evidence

ORD record
ord-60569d70aaab452487a1c490c2ea6585
Source dataset
uspto-grants-2009_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07482345B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes