Ammonium Chloride → 7-[(4-Fluorophenyl)methoxy]-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

HRID 1988835Notes

Reaction equation

[F:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][O:7][C:8]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2[N+:14]([O-])=O)=[CH:4][CH:3]=1.[CH3:19][C:20]([Mg]Br)=[CH:21][CH3:22].[Cl-].[NH4+]>O1CCCC1>[F:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][O:7][C:8]2[CH:13]=[CH:12][N:11]=[C:10]3[C:20]([CH3:19])=[C:21]([CH3:22])[NH:14][C:9]=23)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: -20 °C

Procedure

4-(4-Fluorobenzyloxy)-3-nitropyridine (4.8 g, 19.34 mmol) prepared in Preparation 2 was dissolved in anhydrous tetrahydrofuran (200 ml) under a nitrogen atmosphere. 1-Methyl-1-propenyl magnesium bromide (0.5M in tetrahydrofuran solution, 116 ml, 58.02 mmol) was added at −78° C. to the solution, which was then stirred for 5 hours at −20° C. 20% Ammonium chloride solution (20 ml) was added to the reaction mixture, which was then extracted with ethyl acetate (200 ml) twice. The separated organic layer was dried on anhydrous magnesium sulfate and then concentrated under reduced pressure. The resulting residue was purified with silica gel column chromatography (ethyl acetate/methylene chloride/methanol=10/10/1, (v/v/v)) to give the titled compound as a pale yellow solid (2.45 g, 28.3%).

Workup

extractionwas then extracted with ethyl acetate (200 ml) twice
dry with materialThe separated organic layer was dried on anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe resulting residue was purified with silica gel column chromatography (ethyl acetate/methylene chloride/methanol=10/10/1, (v/v/v))

Sources & evidence

ORD record: ord-6cbc95870d204aa6bedb8ed13dc0d4bc
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07642269B2

Reaction notes

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