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

HRID 2357601Notes

Reaction equation

HRID 2357601 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]([CH3:17])[CH3:16])=[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:42]1[CH:43]=[C:44]([CH:51]=[CH:52][C:53]=1[CH3:54])[C:45]([NH:47][CH:48]1[CH2:50][CH2:49]1)=[O:46].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:48]1([NH:47][C:45](=[O:46])[C:44]2[CH:51]=[CH:52][C:53]([CH3:54])=[C:42]([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]([CH3:17])[CH3:16])=[N:7][N:6]=[CH:5]4)[CH:43]=2)[CH2:49][CH2:50]1

Participants

12

Reactant 6

HCID 962WaterHCID 10340Sodium CarbonateHCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 211071523-bromo-N-cyclopropyl-4-methylbenzamideHCID 684532906-Bromo-N-(2-(dimethylamino)ethyl)phthalazin-1-amine

Product 1

HCID 11848991N-cyclopropyl-3-(1-(2-(dimethylamino)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-(dimethylamino)ethyl)phthalazin-1-amine (115 mg, 390 μmol), potassium acetate (53 mg, 550 μmol), bis(pinacolato)diboron (139 mg, 550 μmol), and 1,1′-bis(diphenylphosphino)ferrocene-palladium dichloride (29 mg, 40 μmol) were suspended in dioxane (4 mL) and placed in the microwave for I 0 min at 160° C. To the reaction was added a mixture of 3-bromo-N-cyclopropyl-4-methylbenzamide (99 mg, 390 μmol), sodium carbonate-2 M in water (0.29 mL, 0.58 mmol), tetrakis(triphenylphosphine)palladium (45 mg, 40 μmol), and ethyl alcohol (5 mL). The reaction 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× with 20 mL of sodium bicarbonate (saturated, aqueous), dried over sodium sulfate, and concentrated via rotovap to give a crude product. The crude product was purified by chromatography to obtain the title compound. Found MS (ES+): 390(M+H)+.

Workup

  1. customplaced in the microwave for I 0 min at 160° C
  2. additionTo the reaction was added
  3. additionadded to an addition funnel
  4. custompartitioned with sodium bicarbonate (saturated, aqueous)
  5. washThe organic layer was washed 3× with 20 mL of sodium bicarbonate (saturated, aqueous)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated via rotovap
  8. customto give a crude product
  9. customThe crude product was purified by chromatography

Sources & evidence

ORD record
ord-6780259d27384c99a249351142677b57
Source dataset
uspto-grants-2010_07
Patent number
US07759337B2

Reaction notes

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