Ammonium Chloride → N-[1-(1-allyl-2,3-dimethyl-1H-pyrrolo[2,3-c]pyridin-7-yl)-ethyl]-4-fluorophenylamine hydrochloride

HRID 1445040Notes

Reaction equation

HRID 1445040 reaction equation
[CH3:1][Mg]Br.[CH2:4]([N:7]1[C:11]2=[C:12]([CH:16]=[N:17][C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)[N:13]=[CH:14][CH:15]=[C:10]2[C:9]([CH3:25])=[C:8]1[CH3:26])[CH:5]=[CH2:6].[Cl-:27].[NH4+]>C(OCC)C>[ClH:27].[CH2:4]([N:7]1[C:11]2=[C:12]([CH:16]([NH:17][C:18]3[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=3)[CH3:1])[N:13]=[CH:14][CH:15]=[C:10]2[C:9]([CH3:25])=[C:8]1[CH3:26])[CH:5]=[CH2:6]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 67141427N-(1-allyl-2,3-dimethyl-1H-pyrrolo[2,3-c]pyridin-7-ylmethylene)-4-fluorophenylamineHCID 178418573HCID 178418573, compound

Product 1

HCID 67141435N-[1-(1-allyl-2,3-dimethyl-1H-pyrrolo[2,3-c]pyridin-7-yl)-ethyl]-4-fluorophenylamine hydrochloride

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Methylmagnesium bromide (3.0M in ethyl ether solution, 37 μl, 1.12 mmol) was added at 0° C. to a solution of N-(1-allyl-2,3-dimethyl-1H-pyrrolo[2,3-c]pyridin-7-ylmethylene)-4-fluorophenylamine (30 mg, 0.112 mmol) prepared in Step 1 in anhydrous ethyl ether (5 ml). The reaction mixture was stirred for 2 hours at room temperature and then a saturated ammonium chloride solution (5 ml) was added thereto. The reaction mixture was extracted with ethyl acetate (15 ml), dried on anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was purified with silica gel column chromatography (ethyl acetate/n-hexane=1/1, v/v). The resulting yellow oil was dissolved in ethyl acetate, saturated with hydrochloric acid gas, and then filtered. The resulting solid was dried under reduced pressure to give 1.4 mg of the titled compound as a white solid.

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate (15 ml)
  2. dry with materialdried on anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified with silica gel column chromatography (ethyl acetate/n-hexane=1/1
  5. dissolutionThe resulting yellow oil was dissolved in ethyl acetate, saturated with hydrochloric acid gas
  6. filtrationfiltered
  7. customThe resulting solid was dried under reduced pressure

Sources & evidence

ORD record
ord-cbf70f4b544a4b069bdac70376d0a210
Source dataset
uspto-grants-2010_02
Patent number
US07662832B2

Reaction notes

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