Ethyl Acetate → HCID 59515513、化合物

HRID 1160226ノート

反応式

HRID 1160226 の反応式
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

参加物

8

反応物 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 59515525HCID 59515525、化合物HCID 59515569HCID 59515569、化合物

生成物 2

HCID 59515513HCID 59515513、化合物HCID 59515534HCID 59515534、化合物

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-40566a3c5fe54e6f9c6b24e3c29ef899
出典データセット
uspto-grants-2010_10
特許番号
US07816357B2

反応ノート

読み込み中…