Propargyl bromide → 1-(propa-1,2-dienyl)-7-(1,2,3,4-tetrahydroisoquinolin-2-yl)-2,3-dimethyl-1H-pyrrolo[2,3-c]pyridine hydrochloride

HRID 1932358Notes

Reaction equation

HRID 1932358 reaction equation
[H-].[Na+].[CH2:3](Br)[C:4]#[CH:5].[ClH:7].[CH2:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][CH2:10][N:9]1[C:18]1[N:19]=[CH:20][CH:21]=[C:22]2[C:26]([CH3:27])=[C:25]([CH3:28])[NH:24][C:23]=12>O1CCCC1>[ClH:7].[CH:3]([N:24]1[C:23]2=[C:18]([N:9]3[CH2:10][CH2:11][C:12]4[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=4)[CH2:8]3)[N:19]=[CH:20][CH:21]=[C:22]2[C:26]([CH3:27])=[C:25]1[CH3:28])=[C:4]=[CH2:5]

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 24758Sodium hydrideHCID 671411697-(1,2,3,4-tetrahydroisoquinolin-2-yl)-2,3-dimethyl-1H-pyrrolo[2,3-c]pyridine hydrochloride

Product 1

HCID 866152531-(propa-1,2-dienyl)-7-(1,2,3,4-tetrahydroisoquinolin-2-yl)-2,3-dimethyl-1H-pyrrolo[2,3-c]pyridine hydrochlorideYield 6.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (60%; 80 mg, 1.80 mmol) and propargyl bromide (35.6 μl, 1.40 mmol) were added at 0° C. to a solution of 7-(1,2,3,4-tetrahydroisoquinolin-2-yl)-2,3-dimethyl-1H-pyrrolo[2,3-c]pyridine hydrochloride (92.3 mg, 0.33 mol) prepared in Example 468 in anhydrous tetrahydrofuran (10 ml). The reaction mixture was stirred for 12 hours at room temperature. Ice was added to the reaction mixture, which was then extracted with ethyl acetate. The organic layer was dried on anhydrous magnesium sulfate and then concentrated under reduced pressure. The resulting residue was purified with silica gel column chromatography (n-hexane/ethyl acetate=1/1, v/v). The resulting product was dissolved in ethyl acetate, saturated with hydrochloric acid gas, and then filtered to give 32.5 mg of the titled compound as a white solid.

Workup

  1. additionIce was added to the reaction mixture, which
  2. extractionwas then extracted with ethyl acetate
  3. dry with materialThe organic layer was dried on anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified with silica gel column chromatography (n-hexane/ethyl acetate=1/1
  6. dissolutionThe resulting product was dissolved in ethyl acetate, saturated with hydrochloric acid gas
  7. filtrationfiltered

Sources & evidence

ORD record
ord-a8d76ce6abc24936befbdc98b495437a
Source dataset
uspto-grants-2012_05
Patent number
US08188114B2

Reaction notes

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