Potassium Carbonate → HCID 12073477, compound

HRID 749493Notes

Reaction equation

HRID 749493 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[C:15]([C:16]([N:18]([CH3:20])[CH3:19])=[O:17])=[N:14][NH:13][C:12](=[O:21])[C:7]=3[N:8]([CH3:11])[C:9]=2[CH:10]=1.C(=O)([O-])[O-].[K+].[K+].Br[C:29]1[CH:30]=[N:31][C:32]([O:35][CH3:36])=[CH:33][CH:34]=1>CN(C)C=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[C:15]([C:16]([N:18]([CH3:19])[CH3:20])=[O:17])=[N:14][N:13]([C:29]4[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[N:31][CH:30]=4)[C:12](=[O:21])[C:7]=3[N:8]([CH3:11])[C:9]=2[CH:10]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27348955-Bromo-2-methoxypyridineHCID 21948051HCID 21948051, compound

Product 1

HCID 12073477HCID 12073477, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 0.3 g (1.04 mmol) of 7-fluoro-N,N,5-trimethyl-4-oxo-3,5-dihydro-4H-pyridazino[4,5-b]-indole-1-carboxamide (obtained in stage 3.2.), 0.120 g (0.63 mmol) of cuprous iodide, 0.20 g (1.45 mmol) of potassium carbonate and 0.60 g (3.19 mmol) of 3-bromo-6-methoxypyridine in 50 ml of N,N-dimethylformamide is heated at 150° C. for 20 h. The reaction mixture is cooled and concentrated under reduced pressure. Dichloromethane, water and a sodium hydroxide solution (1M) are added. The organic phase is separated by settling, washed with water, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue is purified by chromatography on a column of silica gel (eluent: dichloromethane/ethyl acetate: 100/0 to 0/100; then ethyl acetate/methanol: 95/5). The white solid obtained is recrystallized from a dichloromethane/ethyl acetate mixture and washed with diethyl ether. A white solid (0.26 g; 0.66 mmol) is isolated.

Workup

  1. temperatureThe reaction mixture is cooled
  2. concentrationconcentrated under reduced pressure
  3. additionDichloromethane, water and a sodium hydroxide solution (1M) are added
  4. customThe organic phase is separated
  5. washwashed with water
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue is purified by chromatography on a column of silica gel (eluent
  10. customThe white solid obtained
  11. customis recrystallized from a dichloromethane/ethyl acetate mixture
  12. washwashed with diethyl ether
  13. customA white solid (0.26 g; 0.66 mmol) is isolated

Sources & evidence

ORD record
ord-48b352a0429a46cb84f6c65270e17567
Source dataset
uspto-grants-2008_07
Patent number
US07402682B2

Reaction notes

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