Cesium carbonate → HCID 131728823, compound

HRID 546787Notes

Reaction equation

HRID 546787 reaction equation
[CH:1]([NH:3][C:4]1[CH:5]=[CH:6][C:7](/[CH:12]=[CH:13]/[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[N:8][C:9]=1[O:10][CH3:11])=[O:2].C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:27][O:28][CH:29]([O:32][CH3:33])[CH2:30]Br>CN(C=O)C>[CH3:27][O:28][CH:29]([O:32][CH3:33])[CH2:30][C:1]([NH:3][C:4]1[CH:5]=[CH:6][C:7](/[CH:12]=[CH:13]/[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[N:8][C:9]=1[O:10][CH3:11])=[O:2]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 816722-Bromo-1,1-dimethoxyethaneHCID 87216247HCID 87216247, compound

Product 1

HCID 131728823HCID 131728823, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

tert-Butyl (E)-3-(5-formylamino-6-methoxypyridin-2-yl)acrylate synthesized according to the method in Examples 168 and 169 (4 g) was dissolved in DMF (60 mL). Cesium carbonate (9.38 g) was added and the reaction solution was heated to 60° C. Bromoacetaldehyde dimethylacetal (2.08 mL) was added to the reaction solution. The reaction solution was stirred for two hours, heated to 110° C. and stirred for 10 hours. The reaction solution was left to cool. Ice water was added under ice-cooling, followed by extraction with ethyl acetate. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (carrier: Chromatorex Si; elution solvent: heptane:ethyl acetate=7:1→heptane:ethyl acetate=1:2) to obtain the title compound (3.99 g). The property values of the compound are as follows.

Workup

  1. temperatureheated to 110° C.
  2. stirringstirred for 10 hours
  3. waitThe reaction solution was left
  4. temperatureto cool
  5. temperaturecooling
  6. extractionfollowed by extraction with ethyl acetate
  7. dry with materialThe organic layer was dried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel chromatography (carrier: Chromatorex Si; elution solvent: heptane:ethyl acetate=7:1→heptane:ethyl acetate=1:2)

Sources & evidence

ORD record
ord-10b5c901022c48dd9b98f5925e2e1176
Source dataset
uspto-grants-2011_05
Patent number
US07935815B2

Reaction notes

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