Ethyl Acetate → HCID 59515513, 화합물

HRID 1160226노트

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HRID 1160226 반응식
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

참가 물질

8

반응물 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 59515525HCID 59515525, 화합물HCID 59515569HCID 59515569, 화합물

생성물 2

HCID 59515513HCID 59515513, 화합물HCID 59515534HCID 59515534, 화합물

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 1140Toluene용매

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온도
100 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-40566a3c5fe54e6f9c6b24e3c29ef899
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07816357B2

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