Ammonium Chloride → 2-(5-fluoro-2,3-dimethyl-1H-pyrrolo[2,3-c]pyridin-7-yl)-1,2,3,4-tetrahydroisoquinoline

HRID 1932375Notes

Reaction equation

HRID 1932375 reaction equation
[CH3:1][C:2]([Mg]Br)=[CH:3][CH3:4].[F:7][C:8]1[N:13]=[C:12]([N:14]2[CH2:23][CH2:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:15]2)[C:11]([N+:24]([O-])=O)=[CH:10][CH:9]=1.[Cl-].[NH4+]>O1CCCC1>[F:7][C:8]1[CH:9]=[C:10]2[C:3]([CH3:4])=[C:2]([CH3:1])[NH:24][C:11]2=[C:12]([N:14]2[CH2:23][CH2:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:15]2)[N:13]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 671427712-(6-Fluoro-3-nitropyridin-2-yl)-1,2,3,4-tetrahydroisoquinolineHCID 178448414HCID 178448414, compound

Product 1

HCID 671421512-(5-fluoro-2,3-dimethyl-1H-pyrrolo[2,3-c]pyridin-7-yl)-1,2,3,4-tetrahydroisoquinolineYield 32%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-Methyl-1-propenyl magnesium bromide (0.5M in tetrahydrofuran solution; 138 ml, 68.9 mmol) was slowly added at −78° C. to a solution of 2-(6-fluoro-3-nitropyridin-2-yl)-1,2,3,4-tetrahydroisoquinoline (5.38 g, 19.7 mmol) prepared in Step 2 in anhydrous tetrahydrofuran (150 ml). The reaction mixture was stirred for 1 hour at the same temperature, slowly warmed to room temperature, and then stirred overnight. 20% (w/v) Ammonium chloride solution was added to the reaction mixture, which was then extracted with ethyl acetate. The resulting organic layer was dried on anhydrous magnesium sulfate and then filtered. The resulting filtrate was concentrated under reduced pressure. The resulting residue was purified with silica gel column chromatography. The resulting product was crystallized with ethyl ether to give the titled compound as red oil. (Yield: 32%)

Workup

  1. stirringstirred overnight
  2. extractionwas then extracted with ethyl acetate
  3. dry with materialThe resulting organic layer was dried on anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe resulting filtrate was concentrated under reduced pressure
  6. customThe resulting residue was purified with silica gel column chromatography
  7. customThe resulting product was crystallized with ethyl ether

Sources & evidence

ORD record
ord-411ea0bd542b481d978895711f56e93d
Source dataset
uspto-grants-2012_05
Patent number
US08188114B2

Reaction notes

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