Potassium Carbonate → (1,4-Dichloro-phthalazin-6-yl)-(3-trifluoromethyl-benzyl)-amine

HRID 1803491Notes

Reaction equation

HRID 1803491 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([NH2:12])=[CH:9][CH:10]=2)[C:5]([Cl:13])=[N:4][N:3]=1.C([O-])([O-])=O.[K+].[K+].[F:20][C:21]([F:31])([F:30])[C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=1)[CH2:25]Br>CN(C=O)C>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([NH:12][CH2:25][C:24]3[CH:27]=[CH:28][CH:29]=[C:22]([C:21]([F:20])([F:30])[F:31])[CH:23]=3)=[CH:9][CH:10]=2)[C:5]([Cl:13])=[N:4][N:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1230611-(Bromomethyl)-3-(trifluoromethyl)benzeneHCID 584472211,4-Dichlorophthalazin-6-amine

Product 1

HCID 86620966(1,4-Dichloro-phthalazin-6-yl)-(3-trifluoromethyl-benzyl)-amineYield 26.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 1,4-dichloro-6-amino-phthalazine (33 mg, 0.154 mmol), K2CO3 (79 mg, 0.57 mmol), DMF (5 mL) and 3-(trifluoromethyl)benzyl bromide (2.0 mL, 0.17 mmol) were heated to 85° C. for 18 h. The reaction was cooled, poured onto water and extracted with EtOAc. The combined organic layers were washed with H2O, brine, dried (Na2SO4) and concentrated. Column chromatography (Hexanes/EtOAc) afforded the desired product (15 mg, 26.3%) as a yellow solid. m/z 372.08 (M+1).

Workup

  1. temperatureThe reaction was cooled
  2. additionpoured onto water
  3. extractionextracted with EtOAc
  4. washThe combined organic layers were washed with H2O, brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-89b9a14426d34bdab5b5f12ee79b5abb
Source dataset
uspto-grants-2013_01
Patent number
US08349836B2

Reaction notes

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