Water → N-cyclopropyl-3-(1-(2-(diethylamino)ethylamino)phthalazin-6-yl)-4-methylbenzamide

HRID 2357602Notes

Reaction equation

HRID 2357602 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([NH:12][CH2:13][CH2:14][N:15]([CH2:18][CH3:19])[CH2:16][CH3:17])=[N:7][N:6]=[CH:5]2.C([O-])(=O)C.[K+].B1(B2OC(C)(C)C(C)(C)O2)OC(C)(C)C(C)(C)O1.Br[C:44]1[CH:45]=[C:46]([CH:53]=[CH:54][C:55]=1[CH3:56])[C:47]([NH:49][CH:50]1[CH2:52][CH2:51]1)=[O:48].C(=O)([O-])[O-].[Na+].[Na+].O>O1CCOCC1.CCOC(C)=O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(O)C>[CH:50]1([NH:49][C:47](=[O:48])[C:46]2[CH:53]=[CH:54][C:55]([CH3:56])=[C:44]([C:2]3[CH:3]=[C:4]4[C:9](=[CH:10][CH:11]=3)[C:8]([NH:12][CH2:13][CH2:14][N:15]([CH2:18][CH3:19])[CH2:16][CH3:17])=[N:7][N:6]=[CH:5]4)[CH:45]=2)[CH2:51][CH2:52]1

Participants

12

Reactant 6

HCID 962WaterHCID 10340Sodium CarbonateHCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 211071523-bromo-N-cyclopropyl-4-methylbenzamideHCID 684546736-bromo-N-(2-(diethylamino)ethyl)phthalazin-1-amine

Product 1

HCID 11848992N-cyclopropyl-3-(1-(2-(diethylamino)ethylamino)phthalazin-6-yl)-4-methylbenzamide

Reagents, catalysts & solvents 5

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
160 °C

Procedure

6-Bromo-N-(2-(diethylamino)ethyl)phthalazin-1-amine (140 mg, 430 μmol), potassium acetate (60 mg, 610 μmol), bis(pinacolato)diboron (150 mg, 610 μmol), and 1,1′-bis(diphenylphosphino)ferrocene-palladium dichloride (32 mg, 40 μmol) were suspended in dioxane (4 mL) and heated in the microwave for 10 min at 160° C. The reaction was added to a mixture of 3-bromo-N-cyclopropyl-4-methylbenzamide (110mg, 430 μmol), sodium carbonate-2 M in water (0.33 mL, 0.65 mmol), tetrakis(triphenylphosphine)palladium (50 mg, 40 μmol), and ethyl alcohol (5 mL), the combination of which was heated in the microwave for 10 min at 160° C. The reaction mixture was diluted with 20 mL of EtOAc, added to an addition funnel and partitioned with sodium bicarbonate (saturated, aqueous). The organic layer was washed 3 times with 20 mL of sodium bicarbonate (saturated, aqueous), dried over sodium sulfate, and concentrated via rotovap to give crude product. The crude was purified by chromatography to obtain the title compound. Found MS (ES+): 418(M+H)+.

Workup

  1. temperaturethe combination of which was heated in the microwave for 10 min at 160° C
  2. additionadded to an addition funnel
  3. custompartitioned with sodium bicarbonate (saturated, aqueous)
  4. washThe organic layer was washed 3 times with 20 mL of sodium bicarbonate (saturated, aqueous)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated via rotovap
  7. customto give crude product
  8. customThe crude was purified by chromatography

Sources & evidence

ORD record
ord-8851b71155524066857ea6901decd24e
Source dataset
uspto-grants-2010_07
Patent number
US07759337B2

Reaction notes

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