Cesium carbonate → HCID 67231009, compound

HRID 876393Notes

Reaction equation

HRID 876393 reaction equation
C([O-])([O-])=O.[Cs+].[Cs+].[OH:7][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:17]=1[N:16]=[C:15]([C:18]1[N:22]3[CH:23]=[CH:24][C:25]([CH2:27][N:28]4[C:36](=[O:37])[C:35]5[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=5)[C:29]4=[O:38])=[CH:26][C:21]3=[N:20][N:19]=1)[CH:14]=[CH:13]2.Br[CH2:40][C:41]([CH3:45])([CH3:44])[CH2:42][OH:43]>CC(N(C)C)=O.CCOC(C)=O.O>[OH:43][CH2:42][C:41]([CH3:45])([CH3:44])[CH2:40][O:7][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:17]=1[N:16]=[C:15]([C:18]1[N:22]3[CH:23]=[CH:24][C:25]([CH2:27][N:28]4[C:36](=[O:37])[C:35]5[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=5)[C:29]4=[O:38])=[CH:26][C:21]3=[N:20][N:19]=1)[CH:14]=[CH:13]2

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 1425013-Bromo-2,2-dimethyl-1-propanolHCID 136400775HCID 136400775, compound

Product 1

HCID 67231009HCID 67231009, compound

Reagents, catalysts & solvents 2

HCID 31374DimethylacetamideSolventHCID 22728543Water ethylacetateSolvent

Conditions

Temperature
100 °C

Procedure

Cs2CO3 (0.513 g, 1.57 mmol) was added to a solution of 2-((3-(8-hydroxyquinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl)methyl)isoindoline-1,3-dione (0.221 g, 0.524 mmol) and 3-bromo-2,2-dimethylpropan-1-ol (0.350 g, 2.10 mmol) in DMA (2 mL). The reaction was sealed and heated at 100° C. and stirred for 30 minutes. The reaction was cooled to ambient temperature and diluted with EtOAc/H2O (2:1). The phases were separated and the aqueous layer was extracted with ethyl acetate. The combined organics were dried over Na2SO4 and concentrated in vacuo. The crude material was purified by flash column chromatography (eluting with a 20:1 mixture of DCM/MeOH), to afford the desired product.

Workup

  1. customThe reaction was sealed
  2. temperatureThe reaction was cooled to ambient temperature
  3. customThe phases were separated
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. dry with materialThe combined organics were dried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe crude material was purified by flash column chromatography (
  8. washeluting with a 20:1 mixture of DCM/MeOH),

Sources & evidence

ORD record
ord-02efc071adbd43feb2a30d2dd0bbad2c
Source dataset
uspto-grants-2015_03
Patent number
US08987251B2

Reaction notes

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