Cesium carbonate → 6-bromo-4-(2-(6-methylpyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)quinoline

HRID 915531Notes

Reaction equation

HRID 915531 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[Br:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[N:14]=[CH:13][CH:12]=[C:11]2[CH2:18][C:19](=[N:27][N:28]1[CH2:32][CH2:31][CH2:30][C:29]1=O)[C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([CH3:26])[N:21]=1>CN(C)C=O>[Br:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[N:14]=[CH:13][CH:12]=[C:11]2[C:18]1[C:19]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([CH3:26])[N:21]=2)=[N:27][N:28]2[CH2:32][CH2:31][CH2:30][C:29]=12

Participants

4

Reactant 2

HCID 10796Cesium carbonateHCID 589588261-[2-(6-Bromo-quinolin-4-yl)-1-(6-methyl-pyridin-2-yl)-ethylideneamino]-pyrrolidin-2-one

Product 1

HCID 219927086-bromo-4-(2-(6-methylpyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)quinolineYield 71.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of (1.2 eq.) cesium carbonate and 1-[2-(6-bromo-quinolin-4-yl)-1-(6-methyl-pyridin-2-yl)-ethylideneamino]-pyrrolidin-2-one (33.3 g, 78.7 mmol) add 300 mL dry N,N-dimethylformamide. Stir the mixture 20 hours at 100° C. The mixture may turn dark during the reaction. Remove the N,N-dimethylformamide in vacuo. Partition the residue between water and methylene chloride. Extract the aqueous portion with additional methylene chloride. Filter the organic solutions through a 300 mL silica plug, eluting with 1.5 L methylene chloride, 1.5 L ethyl acetate and 1.5 L acetone. Combine the appropriate fractions and concentrate in vacuo. Collect the resulting precipitate by filtration to yield 22.7 g (71.2%) of the desired subtitled intermediate as an off-white solid.

Workup

  1. customThe mixture may turn dark during the reaction
  2. customRemove the N,N-dimethylformamide in vacuo
  3. customPartition the residue between water and methylene chloride
  4. extractionExtract the aqueous portion with additional methylene chloride
  5. filtrationFilter the organic solutions through a 300 mL silica plug
  6. washeluting with 1.5 L methylene chloride, 1.5 L ethyl acetate and 1.5 L acetone
  7. concentrationconcentrate in vacuo
  8. customCollect the resulting precipitate
  9. filtrationby filtration

Sources & evidence

ORD record
ord-2e80fd364c16436da07d28d920d80cfc
Source dataset
uspto-grants-2007_09
Patent number
US07265225B2

Reaction notes

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