Ethyl bromoacetate → HCID 89782957, compound

HRID 877444Notes

Reaction equation

HRID 877444 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][N:11]=[C:10]([C:13]([F:16])([F:15])[F:14])[CH:9]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:23]([O:25][C:26](=[O:29])[CH2:27]Br)[CH3:24]>C(#N)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]([CH2:27][C:26]([O:25][CH2:23][CH3:24])=[O:29])[N:11]=[C:10]([C:13]([F:14])([F:16])[F:15])[CH:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 10796Cesium carbonateHCID 178506069HCID 178506069, compound

Product 1

HCID 89782957HCID 89782957, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To 6 g of 34a in acetonitrile (150 mL) was added cesium carbonate (13.5 g, 41 mmol) followed by ethylbromoacetate (1.3 mL, 30 mmol) and the reaction mixture heated to 80° C. for 6 h. On completion, the solvent was removed, water (100 mL) added and the crude reaction mixture extracted with ethyl acetate (50 mL×3). Combined organic layer was washed with brine, dried over sodium sulphate and concentrated. The crude product was purified by column chromatography using 10% ethyl acetate in hexane to afford 35 (2 g, 26%).

Workup

  1. customOn completion, the solvent was removed
  2. additionwater (100 mL) added
  3. customthe crude reaction mixture
  4. extractionextracted with ethyl acetate (50 mL×3)
  5. washCombined organic layer was washed with brine
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated
  8. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-b48289a960964a67a0c68b2b6d0424f2
Source dataset
uspto-grants-2015_03
Patent number
US08987318B2

Reaction notes

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