Cesium carbonate → 6-(N'-tert-Butoxycarbonylhydrazino)-2-(2-chlorophenylamino)-3,4-difluorobenzoic acid methyl ester

HRID 1723693Notes

Reaction equation

HRID 1723693 reaction equation
[C:1]([O:5][C:6](=[O:9])[NH:7][NH2:8])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[Cs+].[Cs+].[CH3:16][O:17][C:18](=[O:36])[C:19]1[C:24](Br)=[CH:23][C:22]([F:26])=[C:21]([F:27])[C:20]=1[NH:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[Cl:35]>C1(C)C=CC=CC=1.C(Cl)Cl.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].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]>[CH3:16][O:17][C:18](=[O:36])[C:19]1[C:24]([NH:8][NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:9])=[CH:23][C:22]([F:26])=[C:21]([F:27])[C:20]=1[NH:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[Cl:35]

Participants

8

Reactant 3

HCID 10796Cesium carbonateHCID 70091tert-Butyl carbazateHCID 865985926-Bromo-2-(2-chlorophenylamino)-3,4-difluorobenzoic acid methyl ester

Product 1

HCID 865985976-(N'-tert-Butoxycarbonylhydrazino)-2-(2-chlorophenylamino)-3,4-difluorobenzoic acid methyl ester

Reagents, catalysts & solvents 4

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

Pd2(dba)3 (4 mol %), t-butylcarbazate (4.00 equivalents), dppf (12 mol %) and Cs2CO3 (1.00 equivalent) are added to a solution of 6-bromo-2-(2-chlorophenylamino)-3,4-difluorobenzoic acid methyl ester (1.00 equivalent) in PhMe. The reaction mixture is heated in a sealed vial charged under a N2 atmosphere to 100° C. and stirred for 16 hours. After cooling to room temperature, the reaction mixture is diluted with methylene chloride and filtered. The filtrate is concentrated under reduced pressure. The product is purified by trituration or flash column chromatography if further purification is necessary.

Workup

  1. temperatureThe reaction mixture is heated in a sealed
  2. additionvial charged under a N2 atmosphere to 100° C.
  3. filtrationfiltered
  4. concentrationThe filtrate is concentrated under reduced pressure
  5. customThe product is purified by trituration or flash column chromatography if further purification

Sources & evidence

ORD record
ord-31c15461766f4f7a89b38e72d2c8e80e
Source dataset
uspto-grants-2009_02
Patent number
US07485643B2

Reaction notes

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