Cesium carbonate → HCID 68596094, compound

HRID 1496643Notes

Reaction equation

HRID 1496643 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([Cl:14])=[C:6]([NH:8][NH:9][C:10]([O:12][CH3:13])=[O:11])[CH:7]=1.[F:15][C:16]([F:28])([F:27])[O:17][C:18]1[CH:19]=[C:20](B(O)O)[CH:21]=[CH:22][CH:23]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1.CO.C(OCC)C.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]>[Cl:14][C:5]1[CH:4]=[CH:3][C:2]([C:20]2[CH:21]=[CH:22][CH:23]=[C:18]([O:17][C:16]([F:15])([F:27])[F:28])[CH:19]=2)=[CH:7][C:6]=1[NH:8][NH:9][C:10]([O:12][CH3:13])=[O:11]

Participants

9

Reactant 4

HCID 10796Cesium carbonateHCID 11776TriphenylphosphineHCID 27343853-(Trifluoromethoxy)phenylboronic Acid (contains varying amounts of Anhydride)HCID 68595216methyl N-(5-bromo-2-chloro-anilino)carbamate2×

Product 1

HCID 68596094HCID 68596094, compound

Reagents, catalysts & solvents 4

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 887MethanolSolventHCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of methyl 2-(5-bromo-2-chlorophenyl)hydrazine carboxylate (i.e. the product of Step B) (1.27 g, 4.5 mmol), [3-(trifluoromethoxy)phenyl]boronic acid (1.85 g, 9 mmol), cesium carbonate (2.9 g, 9 mmol), tris(dibenzylideneacetone)dipalladium (0.18 g, 0.2 mmol) and triphenylphosphine (1.2 g, 4.5 mmol) in toluene (60 mL) and methanol (60 mL) was heated at refluxed for 24 h. After cooling, the reaction mixture was taken up in diethyl ether and washed with water. After drying over sodium sulfate, the solvent was removed under reduced pressure. The residue was purified by flash chromatography using 25% ethyl acetate in hexanes as eluant to afford a solid matieral (1.3 g), which was a mixture of starting material and the title compound.

Workup

  1. temperaturewas heated
  2. temperatureat refluxed for 24 h
  3. temperatureAfter cooling
  4. washwashed with water
  5. dry with materialAfter drying over sodium sulfate
  6. customthe solvent was removed under reduced pressure
  7. customThe residue was purified by flash chromatography
  8. customto afford a solid matieral (1.3 g), which
  9. additiona mixture of starting material

Sources & evidence

ORD record
ord-cc598027dc2d4899a7f5e2d321b3fa32
Source dataset
uspto-grants-2015_12
Patent number
US09198433B2

Reaction notes

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