Cesium carbonate → HCID 60658785, compound

HRID 707056Notes

Reaction equation

HRID 707056 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]([O:9][CH3:10])=[O:8])[CH2:3][CH2:2]1.Br[C:12]1[S:13][CH:14]=[CH:15][N:16]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C)C=O>[S:13]1[CH:14]=[CH:15][N:16]=[C:12]1[N:1]1[CH2:6][CH2:5][CH:4]([C:7]([O:9][CH3:10])=[O:8])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 764302-BromothiazoleHCID 424914Methyl isonipecotate

Product 1

HCID 60658785HCID 60658785, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of methyl piperidine-4-carboxylate (2.045 g), 2-bromothiazole (1.64 g), and Cs2CO3 (5.86 g) in dimethylformamide (15 mL) was heated at 100° C. overnight. After it cooled to room temperature, the reaction mixture was partitioned between water and ethyl acetate. The organic layer was separated, and the aqueous layer was extracted with additional ethyl acetate three times. The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated. The residue was purified by flash chromatography on silica gel to give the title compound.

Workup

  1. temperatureAfter it cooled to room temperature
  2. customthe reaction mixture was partitioned between water and ethyl acetate
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with additional ethyl acetate three times
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-10375cef595c44be968123e91b1f139f
Source dataset
uspto-grants-2015_11
Patent number
US09174982B2

Reaction notes

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