Sodium Methoxide → HCID 59435979, compound

HRID 1802478Notes

Reaction equation

HRID 1802478 reaction equation
[Br:1][C:2]1[CH:26]=[CH:25][C:5]2[N:6]=[C:7]([NH:15][C:16]3[C:21]([Cl:22])=[CH:20][C:19]([I:23])=[CH:18][C:17]=3[Cl:24])[C:8]3[C:13]([C:4]=2[CH:3]=1)=[C:12](Cl)[N:11]=[CH:10][CH:9]=3.[CH3:27][O-:28].[Na+]>CO.O>[Br:1][C:2]1[CH:26]=[CH:25][C:5]2[N:6]=[C:7]([NH:15][C:16]3[C:21]([Cl:22])=[CH:20][C:19]([I:23])=[CH:18][C:17]=3[Cl:24])[C:8]3[C:13]([C:4]=2[CH:3]=1)=[C:12]([O:28][CH3:27])[N:11]=[CH:10][CH:9]=3

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 594359979-Bromo-1-chloro-N-(2,6-dichloro-4-iodophenyl)benzo[c]-2,6-naphthyridin-5-amine

Product 1

HCID 59435979HCID 59435979, compound

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 887MethanolSolvent

Procedure

To a solution of 9-bromo-1-chloro-N-(2,6-dichloro-4-iodophenyl)benzo[c]-2,6-naphthyridin-5-amine (1.56 g, 2.69 mmol) in methanol (30 mL) was added sodium methoxide (10 mL, 25% in methanol) and heated the reaction to 100° C. for 45min. The reaction was cooled to room temperature and a few drops of water were added to quench the reaction. The organic layer was evaporated under vacuum and the residue was diluted with ethyl acetate and extracted with water. The organic layer was separated, dried with sodium sulfate, filtered and evaporated. The residue was taken to the next step without purification.

Workup

  1. temperatureheated
  2. customthe reaction to 100° C. for 45min
  3. customto quench
  4. customthe reaction
  5. customThe organic layer was evaporated under vacuum
  6. additionthe residue was diluted with ethyl acetate
  7. extractionextracted with water
  8. customThe organic layer was separated
  9. dry with materialdried with sodium sulfate
  10. filtrationfiltered
  11. customevaporated
  12. customThe residue was taken to the next step without purification

Sources & evidence

ORD record
ord-d399cf71e31048a5be52dc6f2970457b
Source dataset
uspto-grants-2013_01
Patent number
US08349865B2

Reaction notes

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