HCID 59683257, compound → HCID 59683267, compound

HRID 2061484Notes

Reaction equation

HRID 2061484 reaction equation
[F:1][C:2]1[C:7]([F:8])=[C:6]([CH3:9])[CH:5]=[C:4](I)[C:3]=1[NH:11][C:12]([NH:14][CH:15]1[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]1)=[O:13]>O1CCOCC1.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].C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[F:1][C:2]1[C:3]2[NH:11][C:12](=[O:13])[N:14]([CH:15]3[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]3)[C:4]=2[CH:5]=[C:6]([CH3:9])[C:7]=1[F:8]

Participants

5

Reactant 1

HCID 59683257HCID 59683257, compound2×

Product 1

HCID 59683267HCID 59683267, compound

Reagents, catalysts & solvents 3

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent2×

Procedure

1,1-dimethylethyl 4-({[(2,3-difluoro-6-iodo-4-methylphenyl)amino]carbonyl}amino)-1-piperidine-carboxylate D21 was dissolved in 1 ml dioxan. Under an argon atmosphere, a mixture of 1,4-dioxane (3 ml), Pd2 dba3 (35 mg, 0.4 mmol), NatBuO (120 mg, 1.20 mmol), and 1,1′-bis(diphenylphosphino)ferrocene (21 mg, 0.4 mmol) was stirred for 10 minutes at room temperature and then 1,1-dimethylethyl 4-({[(2,3-difluoro-6-iodo-4-methylphenyl)amino]carbonyl}amino)-1-piperidine-carboxylate D21 (300 mg) was added and the mixture heated at 80° C. for 2 h. The reaction mixture was cooled to room temperature, quenched with NH4Cl (saturated solution) and extracted with ethyl acetate, Drying (MgSO4), evaporation, and crystallisation from diethyl ether gave 150 mg of the title compound. M−−H=366.

Workup

  1. temperaturethe mixture heated at 80° C. for 2 h
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customquenched with NH4Cl (saturated solution)
  4. extractionextracted with ethyl acetate
  5. customDrying
  6. custom(MgSO4), evaporation, and crystallisation from diethyl ether

Sources & evidence

ORD record
ord-3aa94174c4d843d590c75eb6d2be3319
Source dataset
uspto-grants-2012_10
Patent number
US08283364B2

Reaction notes

Loading…