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

HRID 1445028Notes

Reaction equation

HRID 1445028 reaction equation
[CH3:1][C:2]([Mg]Br)=[CH:3][CH3:4].[F:7][C:8]1[CH:24]=[CH:23][C:11]([O:12][CH2:13][C:14]2[C:19]([N+:20]([O-])=O)=[CH:18][CH:17]=[CH:16][N:15]=2)=[CH:10][CH:9]=1.[Cl-].[NH4+]>O1CCCC1>[F:7][C:8]1[CH:24]=[CH:23][C:11]([O:12][CH2:13][C:14]2[N:15]=[CH:16][CH:17]=[C:18]3[C:3]([CH3:4])=[C:2]([CH3:1])[NH:20][C:19]=23)=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 671428762-(4-Fluorophenoxymethyl)-3-nitropyridineHCID 178448414HCID 178448414, compound

Product 1

HCID 116087297-(4-fluorophenoxymethyl)-2,3-dimethyl-1H-pyrrolo[2,3-c]pyridineYield 19.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-Methyl-1-propenyl magnesium bromide (0.5 M in tetrahydrofuran solution, 1.7 ml, 0.851 mmol) was added at −78° C. to a solution of 2-(4-fluorophenoxymethyl)-3-nitropyridine (71 mg, 0.284 mmol) prepared in Preparation 1 in anhydrous tetrahydrofuran (5 ml). The reaction mixture was stirred overnight and a saturated ammonium chloride solution was added thereto. The reaction mixture was extracted with ethyl acetate (15 ml). The organic layer washed with water (5 ml), dried on anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was purified with silica gel column chromatography (dichloromethane/n-hexane=2/1, v/v) to give 15 mg of the titled compound as brown oil.

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate (15 ml)
  2. washThe organic layer washed with water (5 ml)
  3. dry with materialdried on anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified with silica gel column chromatography (dichloromethane/n-hexane=2/1

Sources & evidence

ORD record
ord-457341f4d7444676b924db24c1f05a83
Source dataset
uspto-grants-2010_02
Patent number
US07662832B2

Reaction notes

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