Benzoyl chloride → HCID 131724857, compound

HRID 2180254Notes

Reaction equation

HRID 2180254 reaction equation
[C:1](Cl)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.NC1[C:12](Cl)=[N:13][C:14]([Cl:17])=[CH:15][CH:16]=1.C(=O)([O-])[O-:20].[Na+].[Na+].C[C:26]([N:28](C)C)=O>C(Cl)Cl.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:17][C:14]1[NH:13][C:12](=[O:20])[C:1]2[C:16]([CH:15]=1)=[N:28][CH:26]=[C:7]1[C:2]=2[CH:3]=[CH:4][CH:5]=[CH:6]1

Participants

7

Reactant 4

HCID 7412Benzoyl chlorideHCID 10340Sodium CarbonateHCID 31374DimethylacetamideHCID 1128462,6-Dichloro-3-pyridylamine

Product 1

HCID 131724857HCID 131724857, compoundYield 13%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
125 °C

Procedure

Amide 5 was prepared from commercial reagents, benzoyl chloride and 3-amino-2,6-dichloropyridine in DCM in high yield. The desired product 4g was prepared by dissolving amide 5 (4.45 g, 16.7 mmol) in DMA (35 mL) and adding sodium carbonate (1.8g, 16.7 mmol) and palladium acetate (400 mg, catalytic amt.). The reaction mixture was heated to 125° C. for several hours until the starting material was no longer present by TLC. The reaction was then cooled down to room temperature and concentrated in vacuo and the crude residue was suspended in boiling EtOAc (100 mL) and filtered through a plug of celite. The filtrate was concentrated and the solid that precipitated out was filtered off and determined to be compound 4g (520 mg, 13% yield). Mp=285-295 (dec.) ° C.; 1H NMR (d6-DMSO) δ 11.92 (bs, 1H), 8.62 (d, 1H), 8.32 (d, 1H), 7.95 (t, 1H), 7.77 (m, 2H), 7.62 (d, 1H). Anal Calcd. for C12H7ClN2O: C, 62.49; H, 3.06; N, 12.15. Found: C, 61.40; H, 3.19; N, 11.77.

Workup

  1. customThe desired product 4g was prepared
  2. temperatureThe reaction was then cooled down to room temperature
  3. concentrationconcentrated in vacuo
  4. filtrationfiltered through a plug of celite
  5. concentrationThe filtrate was concentrated
  6. customthe solid that precipitated out
  7. filtrationwas filtered off

Sources & evidence

ORD record
ord-182a6d2feea04b5e8ce54e6af2641f35
Source dataset
uspto-grants-2005_05
Patent number
US06887996B2

Reaction notes

Loading…