4-Bromopyridinium chloride → HCID 53932915, compound

HRID 2297503Notes

Reaction equation

HRID 2297503 reaction equation
[C:1]([C:3]1[C:12]([O:13][CH3:14])=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[N:6][NH:7][C:8]2=[O:15])#[CH:2].Cl.Br[C:18]1[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=1>C(NCC)C.O.[Cu]I>[CH3:14][O:13][C:12]1[C:3]([C:1]#[C:2][C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:15])[NH:7][N:6]=[CH:5]2

Participants

6

Reactant 2

HCID 881004-Bromopyridinium chlorideHCID 18381652HCID 18381652, compound

Product 1

HCID 53932915HCID 53932915, compoundYield 86%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 8021DiethylamineSolvent

Conditions

Temperature
75 °C

Procedure

A suspension of 5-ethynyl-6-methoxy-2H-phthalazin-1-one (1.9 g, 9.49 mmoles), prepared as described in example 140, 4-bromopyridine hydrochloride (2.214 g, 11.39 mmoles), bis(triphenylphosphine)PdCl2 (133 mg, 0.1998 mmole) and CuI (36 mg, 0.1898 mmole) in diethylamine (40 ml) was heated at 75° C. for 1 hour, cooled, diluted with water (40 ml) and the solid was filtered after 30 minutes under stirring. The solid was suspended in acetone, stirred for 15 minutes, filtered again and dried in oven at 45° C. under vacuum giving 2.263 g of the title compound (yield: 86%).

Workup

  1. customprepared
  2. temperaturecooled
  3. filtrationthe solid was filtered after 30 minutes
  4. stirringstirred for 15 minutes
  5. filtrationfiltered again
  6. customdried in oven at 45° C. under vacuum

Sources & evidence

ORD record
ord-430dabd7d80a46aea53d70964e237509
Source dataset
uspto-grants-2002_12
Patent number
US06492360B1

Reaction notes

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