Cesium carbonate → HCID 90410005、化合物

HRID 626599ノート

反応式

HRID 626599 の反応式
Cl[C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:10]=[N:11][C:12]([N+:15]([O-:17])=[O:16])=[CH:13][CH:14]=2)[CH:5]=[CH:4][N:3]=1.[CH2:18]([N:25]1[CH2:30][CH2:29][N:28]([C:31]([NH2:33])=[O:32])[CH2:27][CH2:26]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.CCOC(C)=O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C>[CH2:18]([N:25]1[CH2:26][CH2:27][N:28]([C:31]([NH:33][C:2]2[CH:7]=[C:6]([O:8][C:9]3[CH:10]=[N:11][C:12]([N+:15]([O-:17])=[O:16])=[CH:13][CH:14]=3)[CH:5]=[CH:4][N:3]=2)=[O:32])[CH2:29][CH2:30]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

参加物

8

反応物 3

HCID 10796Cesium carbonateHCID 8518614-benzylpiperazine-1-carboxamideHCID 593227792-Chloro-4-((6-nitropyridin-3-yl)oxy)pyridine

生成物 1

HCID 90410005HCID 90410005、化合物収率 66.5%

試薬・触媒・溶媒 4

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl触媒HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
120 °C

実験手順

A suspension of Example A1 (0.5 g, 1.987 mmol), 4-benzylpiperazine-1-carboxamide (0.741 g, 3.38 mmol), cesium carbonate (0.971 g, 2.98 mmol) and X-Phos (0.047 g, 0.099 mmol) in dioxane (20 mL) was purged 5 min with Ar. To the reaction mixture was added Pd2 dba3 (0.055 g, 0.060 mmol) and it was then heated to 120° C. After 16 h, the reaction was cooled to RT, diluted with EtOAc (100 mL) and filtered through diatomaceous earth. The filter cake was washed with additional EtOAc and the combined filtrates concentrated to afford crude product. This was purified by silica gel chromatography (0-8% MeOH/DCM) to afford 4-benzyl-N-(4-((6-nitropyridin-3-yl)oxy)pyridin-2-yl)piperazine-1-carboxamide (0.574 g, 66%). 1H NMR (400 MHz, DMSO-d6): δ 9.41 (s, 1H), 8.56 (d, J=2.8 Hz, 1H), 8.40 (d, J=8.9 Hz, 1H), 8.23 (d, J=5.7 Hz, 1H), 7.94 (dd, J=8.9, 2.8 Hz, 1H), 7.55 (d, J=2.3 Hz, 1H), 7.30-7.29 (m, 5H), 6.79 (dd, J=5.7, 2.4 Hz, 1H), 3.47 (s, 2H), 3.43 (t, J=4.7 Hz, 4H), 2.32 (t, J=4.7 Hz, 4H); MS (ESI) m/z: 435.2 (M+H+).

後処理

  1. temperaturethe reaction was cooled to RT
  2. filtrationfiltered through diatomaceous earth
  3. washThe filter cake was washed with additional EtOAc
  4. concentrationthe combined filtrates concentrated
  5. customto afford crude product
  6. customThis was purified by silica gel chromatography (0-8% MeOH/DCM)

出典と根拠

ORDレコード
ord-bba4116e947240ffa3b5e64c92c2d326
出典データセット
uspto-grants-2016_04
特許番号
US09309224B2

反応ノート

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