1,4-Dichlorophthalazine → HCID 86614168, compound

HRID 2361080Notes

Reaction equation

HRID 2361080 reaction equation
[CH3:1][N:2]([CH3:6])[CH2:3][C:4]#[CH:5].[Cl:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11](Cl)=[N:10][N:9]=1>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I.C(#N)C>[Cl:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([C:5]#[C:4][CH2:3][N:2]([CH3:6])[CH3:1])=[N:10][N:9]=1

Participants

6

Reactant 2

HCID 784901,4-DichlorophthalazineHCID 81643N,N-Dimethylpropargylamine

Product 1

HCID 86614168HCID 86614168, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

A resealable pressure bottle was charged with dichlorobis(triphenyl-phosphine)palladium(II) (106 mg, 0.15 mmol), N,N-dimethylprop-2-yn-1-amine (0.13 ml, 1.5 mmol), 1,4-dichlorophthalazine (300 mg, 1.5 mmol), copper(I) iodide (29 mg, 0.15 mmol), TEA (4.2 mL, 30.1 mmol), and ACN (15.0 mL, 0.1M). The vessel was sealed and the mixture was stirred at overnight at 90° C. Next day the reaction was cooled to RT, filtered over celite, and the filtrate was concentrated under reduced pressure to afford a brown residue, which was purified by ISCO silica gel chromatography (5%-7% of 90/10/1 DCM/MeOH/NH4OH to afford 3-(4-chlorophthalazin-1-yl)-N,N-dimethylprop-2-yn-1-amine. MS m/z=246 [M+1]+. Calc'd for C13H12ClN3: 245.7.

Workup

  1. customThe vessel was sealed
  2. temperatureNext day the reaction was cooled to RT
  3. filtrationfiltered over celite
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customto afford a brown residue, which
  6. customwas purified by ISCO silica gel chromatography (5%-7% of 90/10/1 DCM/MeOH/NH4OH

Sources & evidence

ORD record
ord-5ea640872299481882198e5bdfaf5ebc
Source dataset
uspto-grants-2014_04
Patent number
US08686155B2

Reaction notes

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