4-Bromopyridinium chloride → HCID 18332458, compound

HRID 2268935Notes

Reaction equation

HRID 2268935 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.BrC1[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]([CH2:1][C:2]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 18332458HCID 18332458, compoundYield 89.2%

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-e76187faf1ab46b0bd859957dda51b2d
Source dataset
uspto-grants-2001_12
Patent number
US06329370B1

Reaction notes

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