Ethyl Acetate → HCID 59515513, compound

HRID 1160226Notes

Reaction equation

HRID 1160226 reaction equation
C([N:8]1[C:13](=O)[C:12]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)=C(Cl)C(OCC2C=CC=CC=2)=N1)C1C=CC=CC=1.[CH2:31]([N:38]1[C:43](=[O:44])[C:42](Cl)=[C:41]([C:46]2[CH:51]=[CH:50][C:49]([Cl:52])=[CH:48][CH:47]=2)[C:40]([O:53][CH2:54][C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)=[N:39]1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.C(=O)([O-])[O-].[Na+].[Na+].C(O[CH2:71][CH3:72])(=O)C>C1(C)C=CC=CC=1.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>[CH2:31]([N:38]1[C:43](=[O:44])[C:42]([C:15]2[CH:16]=[CH:17][C:18]([Cl:21])=[CH:19][CH:20]=2)=[C:41]([C:72]2[CH:71]=[CH:43][N:38]=[CH:31][CH:32]=2)[C:40]([O:53][CH2:54][C:55]2[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=2)=[N:39]1)[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1.[CH2:31]([N:38]1[C:43](=[O:44])[C:42]([C:15]2[CH:12]=[CH:13][N:8]=[CH:19][CH:20]=2)=[C:41]([C:46]2[CH:51]=[CH:50][C:49]([Cl:52])=[CH:48][CH:47]=2)[C:40]([O:53][CH2:54][C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)=[N:39]1)[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 59515525HCID 59515525, compoundHCID 59515569HCID 59515569, compound

Product 2

HCID 59515513HCID 59515513, compoundHCID 59515534HCID 59515534, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution the mixture of 2-benzyl-6-(benzyloxy)-5-chloro-4-(4-chlorophenyl)pyridazin-3(2H)-one and 2-benzyl-6-(benzyloxy)-4-chloro-5-(4-chlorophenyl)pyridazin-3(2H)-one (9.9 g, 22.7 mmol), prepared as described in Example 8A, in toluene (136 ml) was added Pd(PPh3)4 (2.35 g, 1.17 mmol). After 2 min, 2N sodium carbonate (45.4 ml, 90.8 mmol) solution was added, followed by 4-(4,4,5,5-tetramethyl-1,3,2-dioxoborolan-2-yl)pyridine (8.5 g, 41.4 mmol). The reaction was stirred at 100° C. for 42 hours. After this time, the reaction mixture was cooled to RT and diluted with ethyl acetate. The resulting solution was washed with water and saturated aqueous NaCl. The organic layer was dried over Na2SO4, filtered and concentrated. The crude product was purified by silica gel column chromatography using an automated system and eluting with a gradient of 20-50% Ethyl acetate-Hexane to give the title compounds 2-benzyl-6-(benzyloxy)-4-(4-chlorophenyl)-5-(pyridin-4-yl)pyridazin-3(2H)-one and 2-benzyl-6-(benzyloxy)-5-(4-chlorophenyl)-4-(pyridin-4-yl)pyridazin-3(2H)-one as a mixture, as light yellow solid (4.5 g, 29% two steps).

Workup

  1. customprepared
  2. temperatureAfter this time, the reaction mixture was cooled to RT
  3. washThe resulting solution was washed with water and saturated aqueous NaCl
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by silica gel column chromatography
  8. washeluting with a gradient of 20-50% Ethyl acetate-Hexane

Sources & evidence

ORD record
ord-40566a3c5fe54e6f9c6b24e3c29ef899
Source dataset
uspto-grants-2010_10
Patent number
US07816357B2

Reaction notes

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