Cesium carbonate → HCID 86677027、化合物

HRID 927078ノート

反応式

HRID 927078 の反応式
[CH2:1]([O:8][C:9]1[N:10]=[N:11][C:12](Cl)=[CH:13][C:14]=1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O1CCOCC1.C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C)C(C)(C)OB([C:44]([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)=[CH2:45])O1>C([P+]([Pd](Cl)(Cl)[P+](C1C=CC(N(C)C)=CC=1)(C(C)(C)C)C(C)(C)C)(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)(C)C.O>[CH2:1]([O:8][C:9]1[N:10]=[N:11][C:12]([C:44]([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)=[CH2:45])=[CH:13][C:14]=1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 312751,4-DioxaneHCID 110316711-Phenylvinylboronic acid, pinacol esterHCID 122134743,4-Bis(benzyloxy)-6-chloropyridazine2 回

生成物 1

HCID 86677027HCID 86677027、化合物収率 91%

試薬・触媒・溶媒 2

HCID 178482902HCID 178482902、化合物触媒HCID 962Water溶媒

反応条件

温度
80 °C

実験手順

A mixture of 3,4-bis(benzyloxy)-6-chloropyridazine (Intermediate 1: 3 g, 9.18 mmol), dioxane (32.1 ml) and water (9.64 ml) was degassed and to this was added mono(bis(di-tert-butyl(4-(dimethylamino)phenyl)phosphonio)palladium(IV)) dichloride (0.195 g, 0.275 mmol), cesium carbonate (10.14 g, 31.1 mmol) and 4,4,5,5-tetramethyl-2-(1-phenylethenyl)-1,3,2-dioxaborolane (3 g, 13.04 mmol). The mixture was heated to 80° C. for 6 hours and upon cooling was partitioned between dichloromethane and water. The organic portion was dried (MgSO4), filtered and concentrated to give an orange oil. The crude oil was purified by silica chromatography eluting with 0-60% ethyl acetate in petrol to afford 3,4-bis(benzyloxy)-6-(1-phenylethenyl)pyridazine as a brown oil (yield=91%).

後処理

  1. customwas degassed
  2. temperatureupon cooling
  3. customwas partitioned between dichloromethane and water
  4. dry with materialThe organic portion was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give an orange oil
  8. customThe crude oil was purified by silica chromatography
  9. washeluting with 0-60% ethyl acetate in petrol

出典と根拠

ORDレコード
ord-383d0179d62c48d9821b288ebf108a23
出典データセット
uspto-grants-2016_03
特許番号
US09290456B2

反応ノート

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