Hydrochloric Acid → HCID 22988002, compound

HRID 429209Notes

Reaction equation

HRID 429209 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][C:9]([C:11]3[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=3)=[CH:10][C:3]=12.Br[C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=1.C(=O)([O-])[O-].[Na+].[Na+].Cl>CN1CCCC1=O.[Cu](Br)Br>[F:24][C:21]1[CH:22]=[CH:23][C:18]([N:8]2[C:4]3=[N:5][CH:6]=[CH:7][C:2]([CH3:1])=[C:3]3[CH:10]=[C:9]2[C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)=[CH:19][CH:20]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 99931-Bromo-4-fluorobenzeneHCID 10340Sodium CarbonateHCID 22987963HCID 22987963, compound

Product 1

HCID 22988002HCID 22988002, compoundYield 6.9%

Reagents, catalysts & solvents 2

HCID 24611Copper bromide (CuBr2)CatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
180 °C

Procedure

To a solution of 4-methyl-2-(pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridine (0.3 g, 1.43 inmol) in N-methylpyrrolidone (5 ml) was added 4-bromofluorobenzene (0.57 ml, 5.2 mmol), copper bromide (0.205 g, 1.43 mmol) and sodium carbonate (0.15 g, 1.43 mmol) and the reaction mixture was heated to 180° C. under argon. After 24 h, the reaction mixture was cooled and poured into 10% hydrochloric acid (50 ml). The solution was filtered through Celite® and the filtrate was neutralized to pH 7 with 10% sodium hydroxide. The solid was filtered off, dissolved in 80% methanol:methylene chloride and purified by preparatory thin layer chromatography to give 1-(4-fluorophenyl)-4-methyl-2-(pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridine (0.03 g) as a tan solid.

Workup

  1. temperaturethe reaction mixture was cooled
  2. filtrationThe solution was filtered through Celite®
  3. filtrationThe solid was filtered off
  4. dissolutiondissolved in 80% methanol
  5. custommethylene chloride and purified by preparatory thin layer chromatography

Sources & evidence

ORD record
ord-56102b93b82443af8322940625a2fb41
Source dataset
uspto-grants-2001_11
Patent number
US06316464B1

Reaction notes

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