HCID 15191520, compound → HCID 86690153, compound

HRID 1500209Notes

Reaction equation

HRID 1500209 reaction equation
[C:1]1([CH3:17])[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[N:12]=[CH:11][C:10]([NH:13]C(=O)C)=[CH:9][CH:8]=2)[CH:2]=1.F[B-](F)(F)F.[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([I+]C2C(C)=CC(C)=CC=2C)=[CH:26][CH:25]=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(O)(=O)C>[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([C:4]2[CH:5]=[CH:6][C:1]([CH3:17])=[CH:2][C:3]=2[C:7]2[N:12]=[CH:11][C:10]([NH2:13])=[CH:9][CH:8]=2)=[CH:26][CH:25]=1

Participants

5

Reactant 2

HCID 15191520HCID 15191520, compound2×HCID 86690154HCID 86690154, compound

Product 1

HCID 86690153HCID 86690153, compoundYield 72.5%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 176Acetic AcidSolvent

Procedure

To acetic acid (17 ml), N-(6-m-tolylpyridine-3-yl)acetamide (0.50 g, 2.2 mmol), (4-chlorophenyl)(2,4,6-trimethylphenyl)iodonium tetrafluoroborate (1.13 g, 2.5 mmol) synthesized in (ii) and palladium acetate (0.025 g, 0.11 mmol) were added, and reacted at 100° C. for 1 hour. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography. The solvent was distilled off under reduced pressure. Methanol and 35% hydrochloric acid were added, and the hydrolysis was carried out at 65° C. for 2 hours. Methanol was distilled off under reduced pressure. Purification by column chromatography gave the title compound (0.47 g, 72.5%).

Workup

  1. additionwere added
  2. customreacted at 100° C. for 1 hour
  3. distillationThe solvent was distilled off under reduced pressure
  4. customthe residue was purified by column chromatography
  5. distillationThe solvent was distilled off under reduced pressure
  6. additionMethanol and 35% hydrochloric acid were added
  7. distillationMethanol was distilled off under reduced pressure
  8. customPurification by column chromatography

Sources & evidence

ORD record
ord-9a40e4ecbd2d465fbd42508590c22819
Source dataset
uspto-grants-2015_12
Patent number
US09206129B2

Reaction notes

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