Potassium Carbonate → HCID 12073479, compound

HRID 749495Notes

Reaction equation

HRID 749495 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[C:15]([C:16]([N:18]4[CH2:22][CH2:21][CH2:20][CH2:19]4)=[O:17])=[N:14][NH:13][C:12](=[O:23])[C:7]=3[N:8]([CH3:11])[C:9]=2[CH:10]=1.C(=O)([O-])[O-].[K+].[K+].Br[C:31]1[N:36]=[CH:35][CH:34]=[CH:33][N:32]=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]4[CH2:22][CH2:21][CH2:20][CH2:19]4)=[O:17])=[N:14][N:13]([C:31]4[N:36]=[CH:35][CH:34]=[CH:33][N:32]=4)[C:12](=[O:23])[C:7]=3[N:8]([CH3:11])[C:9]=2[CH:10]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 783452-BromopyrimidineHCID 21948042HCID 21948042, compound

Product 1

HCID 12073479HCID 12073479, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 0.24 g (0.73 mmol) of 1-[[7-fluoro-5-methyl-4-oxo-3,5-dihydro-4H-pyridazino[4,5-b]indol-1-yl]carbonyl]pyrrolidine (obtained in stage 5.1.), 0.120 g (0.63 mmol) of cuprous iodide, 0.15 g (1.09 mmol) of potassium carbonate and of 0.30 g (1.89 mmol) of 2-bromopyrimidine in 40 ml of N,N-dimethylformamide is heated at 150° C. for 16 h. The reaction mixture is cooled and concentrated under reduced pressure. Dichloromethane, water and a concentrated sodium hydroxide solution are added. The organic phase is separated by settling, filtered through Celite®, 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: 80/20 to 0/100; ethyl acetate/methanol: 100/0 to 90/10). The solid obtained is recrystallized from a dichloromethane/ethyl acetate mixture and washed with diethyl ether.

Workup

  1. temperatureThe reaction mixture is cooled
  2. concentrationconcentrated under reduced pressure
  3. additionDichloromethane, water and a concentrated sodium hydroxide solution are added
  4. customThe organic phase is separated
  5. filtrationfiltered through Celite®
  6. washwashed with water
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residue is purified by chromatography on a column of silica gel (eluent: dichloromethane/ethyl acetate: 80/20 to 0/100; ethyl acetate/methanol: 100/0 to 90/10)
  11. customThe solid obtained
  12. customis recrystallized from a dichloromethane/ethyl acetate mixture
  13. washwashed with diethyl ether

Sources & evidence

ORD record
ord-a0e7206caa894dafa4abe8431982b2c6
Source dataset
uspto-grants-2008_07
Patent number
US07402682B2

Reaction notes

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