Cesium carbonate → HCID 67044808, compound

HRID 1944464Notes

Reaction equation

HRID 1944464 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[SH:16])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].BrC1[CH:19]=[CH:20][CH:21]=[N:22][CH:23]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C[N:31]1CCCC1=O>O>[Si:1]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[S:16][C:20]1[CH:21]=[N:22][CH:23]=[N:31][CH:19]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 122863-BromopyridineHCID 13387N-methyl-2-pyrrolidoneHCID 12163352HCID 12163352, compound

Product 1

HCID 67044808HCID 67044808, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-(tert-butyl-dimethylsilanyloxymethyl)benzenethiol (5.6 g), 5-bromopyridine (4.6 g), cesium carbonate (11 g) and N-methylpyrrolidone (25 mL) was heated at 100° C. for 2 hours. The mixture was diluted with water and extracted with diethyl ether. The combined organic extract was washed with water and saturated aqueous sodium chloride solution and dried over magnesium sulfate. The solvent was removed under reduced pressure and the residue was purified by column chromatography on silica gel, eluting with a mixture of cyclohexane and ethyl acetate (1:0 to 0:1 by volume) to afford the title compound as a light brown oil (7.0 g).

Workup

  1. extractionextracted with diethyl ether
  2. extractionThe combined organic extract
  3. washwas washed with water and saturated aqueous sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was purified by column chromatography on silica gel
  7. washeluting with a mixture of cyclohexane and ethyl acetate (1:0 to 0:1 by volume)

Sources & evidence

ORD record
ord-042e37cf58c44b538e50c2af690e1c84
Source dataset
uspto-grants-2013_03
Patent number
US08394836B2

Reaction notes

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