Propargyl bromide → HCID 85969570, compound

HRID 1916717Notes

Reaction equation

HRID 1916717 reaction equation
[H-].[Na+].[NH:3]1[C:11]2[C:6](=[CH:7][C:8]([CH:12]=[O:13])=[CH:9][CH:10]=2)[CH:5]=[CH:4]1.[CH2:14](Br)[C:15]#[CH:16]>C1COCC1>[CH2:16]([N:3]1[C:11]2[C:6](=[CH:7][C:8]([CH:12]=[O:13])=[CH:9][CH:10]=2)[CH:5]=[CH:4]1)[C:15]#[CH:14]

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 24758Sodium hydrideHCID 589040Indole-5-carboxaldehyde

Product 1

HCID 85969570HCID 85969570, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

0.65 g (50% in mineral oil, 13.5 mmol) NaH are batchwise added to a solution, cooled to 0° C., of 2.0 g (13.5 mmol) 1H-indole-5-carbaldehyde in 80 mL THF and after heating to RT stirred for 15 min. Then a solution of 1.6 mL (80% in toluene, 15 mmol) propargyl bromide in 20 mL THF is slowly added dropwise and the reaction mixture is stirred overnight at RT. The mixture is evaporated down i. vac., the residue is combined with water, the aqueous phase is exhaustively extracted with EtOAc and the organic phase is dried over Na2SO4. After the desiccant and solvent have been eliminated the residue is purified by chromatography (silica gel, gradient: cyc/EtOAc 4:1 to 2:1).

Workup

  1. stirringthe reaction mixture is stirred overnight at RT
  2. customThe mixture is evaporated down i
  3. extractionthe aqueous phase is exhaustively extracted with EtOAc
  4. dry with materialthe organic phase is dried over Na2SO4
  5. customis purified by chromatography (silica gel, gradient: cyc/EtOAc 4:1 to 2:1)

Sources & evidence

ORD record
ord-a730bd75ea2e461aa8d84ce46434ed77
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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