Acetamide → HCID 87192560、化合物

HRID 2089007

反応式

HRID 2089007 の反応式
Cl[C:2]1[CH:7]=[C:6]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[CH:14][CH:15]=3)[N:10]([S:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)(=[O:19])=[O:18])[CH:9]=2)[CH:5]=[C:4]([Cl:26])[N:3]=1.[C:27]([NH2:30])(=[O:29])[CH3:28].C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:26][C:4]1[N:3]=[C:2]([NH:30][C:27](=[O:29])[CH3:28])[CH:7]=[C:6]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[CH:14][CH:15]=3)[N:10]([S:17]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)(=[O:19])=[O:18])[CH:9]=2)[CH:5]=1

参加物

6

反応物 4

HCID 178AcetamideHCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 866498693-(2,6-dichloropyridin-4-yl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

生成物 1

HCID 87192560HCID 87192560、化合物収率 25.2%

試薬・触媒・溶媒 1

HCID 167845palladium(II) acetate触媒

反応条件

温度
85 °C

実験手順

A mixture of Example 7a (1.44 g, 3.57 mmol), acetamide (0.295 g, 4.99 mmol), cesium carbonate (1.743 g, 5.35 mmol), palladium (II) acetate (0.024 g, 0.107 mmol), and Xantphos (0.093 g, 0.161 mmol) was degassed and heated at 85° C. in a sealed vial for 6 hours. The reaction mixture was cooled and concentrated. The residue was treated with 20% brine and extracted with EtOAc (2×). The organic layers were dried, concentrated, and purified on a 40 g column using the ISCO Companion flash system eluting with CH2Cl2/EtOAc (90:10) to give 0.384 g of the title compound.

後処理

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated
  3. additionThe residue was treated with 20% brine
  4. extractionextracted with EtOAc (2×)
  5. customThe organic layers were dried
  6. concentrationconcentrated
  7. custompurified on a 40 g column
  8. washeluting with CH2Cl2/EtOAc (90:10)

出典と根拠

ORDレコード
ord-9cf9dd06848645bfa34fc70ecf343d49
出典データセット
uspto-grants-2013_05
特許番号
US08435980B2

関連ノート

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