4-Fluoroaniline → N-(1-allyl-2,3-dimethyl-1H-pyrrolo[2,3-c]pyridin-7-ylmethylene)-4-fluorophenylamine

HRID 1445039Notes

Reaction equation

HRID 1445039 reaction equation
[CH2:1]([N:4]1[C:8]2=[C:9]([CH:13]=O)[N:10]=[CH:11][CH:12]=[C:7]2[C:6]([CH3:15])=[C:5]1[CH3:16])[CH:2]=[CH2:3].[F:17][C:18]1[CH:24]=[CH:23][C:21]([NH2:22])=[CH:20][CH:19]=1>C(O)C>[CH2:1]([N:4]1[C:8]2=[C:9]([CH:13]=[N:22][C:21]3[CH:23]=[CH:24][C:18]([F:17])=[CH:19][CH:20]=3)[N:10]=[CH:11][CH:12]=[C:7]2[C:6]([CH3:15])=[C:5]1[CH3:16])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 97314-FluoroanilineHCID 866152501-allyl-2,3-dimethyl-1H-pyrrolo[2,3-c]pyridin-7-carbaldehyde

Product 1

HCID 67141427N-(1-allyl-2,3-dimethyl-1H-pyrrolo[2,3-c]pyridin-7-ylmethylene)-4-fluorophenylamineYield 132%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1-allyl-2,3-dimethyl-1H-pyrrolo[2,3-c]pyridin-7-carbaldehyde (1.214 g, 5.67 mmol) prepared in Preparation 3 and 4-fluoroaniline (0.54 ml, 5.67 mmol) in ethanol (10 ml) was refluxed for 1 hour. The reaction mixture was cooled to room temperature and then concentrated under reduced pressure to give 2,3 g of the titled compound as a brown solid. The product was used in the subsequent step without further purification.

Workup

  1. temperaturewas refluxed for 1 hour
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7353d7eb52d24a228006dca798d2d405
Source dataset
uspto-grants-2010_02
Patent number
US07662832B2

Reaction notes

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