Propargyl bromide → HCID 14812561, compound

HRID 2061618Notes

Reaction equation

HRID 2061618 reaction equation
[CH3:1][C:2]1([CH3:8])[NH:6][NH:5][C:4](=[O:7])[CH2:3]1.C([O-])([O-])=O.[K+].[K+].[Li+].[I-].[CH2:17](Br)[C:18]#[CH:19]>C(#N)C>[CH3:1][C:2]1([CH3:8])[N:6]([CH2:19][C:18]#[CH:17])[NH:5][C:4](=[O:7])[CH2:3]1

Participants

6

Reactant 4

HCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 66321Lithium iodideHCID 111160265,5-dimethylpyrazolidin-3-one

Product 1

HCID 14812561HCID 14812561, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 102 (10.0 g, 87.7 mmol) in acetonitrile (100 mL) was added K2CO3 (12.7 g, 92 mmol), LiI (0.59 g, 4.4 mmol) and propargyl bromide (11.0 g, 92 mmol). The resulting reaction mixture was refluxed for 24 h. Progress of the reaction was monitored using TLC. Upon completion of the starting material, the crude reaction mixture was filtered in a small pad of Celite and the solvent was evaporated under vacuum at room temperature. The crude material was passed through column eluting with EtOAc/hexane (3:7) to afford 103 (5.9 g) in 45% yield as a crystalline, pale yellow solid. 1H NMR (CDCl3) δ 7.45 (bs, 1H), 3.53 (d, J=2.2 Hz, 2H), 2.46 (s, 2H), 2.29 (t, J=2.6 Hz, 1H), 1.35 (s, 6H).

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas refluxed for 24 h
  3. customUpon completion of the starting material, the crude reaction mixture
  4. filtrationwas filtered in a small pad of Celite
  5. customthe solvent was evaporated under vacuum at room temperature
  6. washeluting with EtOAc/hexane (3:7)

Sources & evidence

ORD record
ord-5b142d753a8e4659a554c52b993a74f1
Source dataset
uspto-grants-2012_10
Patent number
US08283358B2

Reaction notes

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