Ammonium Chloride → 2,3-dimethyl-7-(4-vinylphenyl)-1H-pyrrolo[2,3-c]pyridine

HRID 1932348Notes

Reaction equation

[N+:1]([C:4]1[C:5]([C:10]2[CH:15]=[CH:14][C:13]([CH:16]=[CH2:17])=[CH:12][CH:11]=2)=[N:6][CH:7]=[CH:8][CH:9]=1)([O-])=O.[CH3:18][C:19]([Mg]Br)=[CH:20][CH3:21].[Cl-].[NH4+]>O1CCCC1>[CH3:18][C:19]1[NH:1][C:4]2=[C:5]([C:10]3[CH:15]=[CH:14][C:13]([CH:16]=[CH2:17])=[CH:12][CH:11]=3)[N:6]=[CH:7][CH:8]=[C:9]2[C:20]=1[CH3:21]

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of 3-nitro-2-(4-vinylphenyl)pyridine (4.9 g, 21.6 mmol) prepared in Preparation 9 in anhydrous tetrahydrofuran (150 ml) was cooled to −78° C. and 1-methyl-1-propenyl magnesium bromide (0.5M in anhydrous tetrahydrofuran solution; 130 ml) was slowly added thereto. 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 reaction mixture was dried on anhydrous magnesium sulfate, filtered, and then concentrated under reduced pressure. The resulting residue was purified with silica gel column chromatography and then crystallized with ethyl ether to give 612 mg of the titled compound as a white solid.

Workup

temperatureslowly warmed to room temperature
stirringstirred overnight
extractionwas then extracted with ethyl acetate
dry with materialThe reaction mixture was dried on anhydrous magnesium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe resulting residue was purified with silica gel column chromatography
customcrystallized with ethyl ether

Sources & evidence

ORD record: ord-10a67566096d423791ef3b2df8a17cc2
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188114B2

Reaction notes

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