Hydrochloric Acid → HCID 22987963, compound

HRID 429208Notes

Reaction equation

HRID 429208 reaction equation
Br[C:2]1[C:3]([N:9]=[C:10]([C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)[CH3:11])=[N:4][CH:5]=[C:6](C)[CH:7]=1.[CH2:18]1N2CCN(CC2)C1.Cl>CN(C)C=O>[CH3:18][C:7]1[CH:6]=[CH:5][N:4]=[C:3]2[NH:9][C:10]([C:12]3[CH:13]=[CH:14][N:15]=[CH:16][CH:17]=3)=[CH:11][C:2]=12

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 9237DabcoHCID 54517970HCID 54517970, compound

Product 1

HCID 22987963HCID 22987963, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of (3-bromo-5-methylpyridin-2-yl)-(1-pyridin-4-ylethylidene)amine (4.25 g, 14.65 mmol) in dimethylformamide (75 ml) was added DABCO® (4.93 g, 43.96 mmol) and], bis-dichlorotriphenylphosphine palladium (0.52 g, 0.73 mmol). The reaction mixture was heated at 120° C. under argon atmosphere. After 1.5 days, the reaction mixture was cooled into room temperature and poured into 10% hydrochloric acid (100 ml). The solution was filtered through Celite® and the filtrate was neutralized to pH 7 with 10% sodium hydroxide and the solid was filtered off to give 4-methyl-2-(pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridine (1.57 g) as a brown solid.

Workup

  1. temperaturethe reaction mixture was cooled into room temperature
  2. filtrationThe solution was filtered through Celite®
  3. filtrationthe solid was filtered off

Sources & evidence

ORD record
ord-4a34f72a1a9e4bcfb74fcf914a94891a
Source dataset
uspto-grants-2001_11
Patent number
US06316464B1

Reaction notes

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