HCID 89704786, compound → HCID 89704911, compound

HRID 928959Notes

Reaction equation

HRID 928959 reaction equation
[N:1]([C:4]1[C:19]([O:20]CC2C=CC=CC=2)=[CH:18][C:7]([C:8]([O:10]CC2C=CC=CC=2)=[O:9])=[C:6]([NH:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[F:35])[C:5]=1[F:36])=[N+]=[N-].[H][H]>CO.[Pd]>[NH2:1][C:4]1[C:19]([OH:20])=[CH:18][C:7]([C:8]([OH:10])=[O:9])=[C:6]([NH:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[F:35])[C:5]=1[F:36]

Participants

5

Reactant 2

HCID 89704786HCID 89704786, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 89704911HCID 89704911, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of benzyl 4-azido-5-benzyloxy-3-fluoro-2-((2-fluorophenyl)amino)benzoate (14.63 g, 30.07 mmol) in MeOH (200 mL) was added and 10% palladium on carbon (2.55 g) under nitrogen atmosphere. Then the nitrogen atmosphere was completely changed to hydrogen atmosphere. The mixture was stirred for 6 h at ambient temperature. After the insoluble matter was filtered off, the solvent was concentrated in vacuo to give the crude product (7.58 g, 90% yield), which was used directly in next step without further purification.

Workup

  1. filtrationAfter the insoluble matter was filtered off
  2. concentrationthe solvent was concentrated in vacuo

Sources & evidence

ORD record
ord-3ea2d5a334864941802c9855842b35f5
Source dataset
uspto-grants-2016_03
Patent number
US09290468B2

Reaction notes

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