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Cesium carbonate → N-[6-Amino-5-(2,3-dichloro-5-methoxyphenyl)pyrazin-2-yl]-1-methyl-1H-pyrazole-5-carboxamide

HRID 2100344
ノート
印刷プレビュー

反応式

HRID 2100344 の反応式
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C:9]([C:11]2[N:15]([CH3:16])[N:14]=[CH:13][CH:12]=2)=[O:10])[CH:5]=[N:4][C:3]=1Cl.[Cl:18][C:19]1[C:24]([Cl:25])=[CH:23][C:22]([O:26][CH3:27])=[CH:21][C:20]=1B1OC(C)(C)C(C)(C)O1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.O>[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C:9]([C:11]2[N:15]([CH3:16])[N:14]=[CH:13][CH:12]=2)=[O:10])[CH:5]=[N:4][C:3]=1[C:20]1[CH:21]=[C:22]([O:26][CH3:27])[CH:23]=[C:24]([Cl:25])[C:19]=1[Cl:18]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 577991422-(2,3-Dichloro-5-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 57799151N-(6-Amino-5-chloropyrazin-2-yl)-1-methyl-1H-pyrazole-5-carboxamide

生成物 1

HCID 16661733N-[6-Amino-5-(2,3-dichloro-5-methoxyphenyl)pyrazin-2-yl]-1-methyl-1H-pyrazole-5-carboxamide収率 46.2%

試薬・触媒・溶媒 2

HCID 962
Water
溶媒
HCID 312751,4-Dioxane溶媒

反応条件

温度
80 °C

実験手順

N-(6-Amino-5-chloropyrazin-2-yl)-1-methyl-1H-pyrazole-5-carboxamide (Preparation 2, 0.1 g, 0.396 mmol) was combined with 2,(2,3-dichloro-5-methoxy-phenyl-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (Preparation 18), (0.156 g, 0.515 mmol), cesium carbonate (0.129 g, 0.396 mmol) and palladium tetrakistriphenylphosphine (0.046 g, 0.04 mmol) and suspended in a mixture of 1,4-dioxane (1 ml) and water (0.5 ml). The reaction was heated at 80° C. for 5 hours. The reaction was allowed to cool to room temperature and then concentrated in vacuo. The residue was partitioned between aqueous sodium carbonate solution (20 ml) and ethyl acetate (20 ml) and the organic layer dried (Na2SO4) and concentrated in vacuo. The residue was purified by silica gel column chromatography, eluting with ethyl acetate:heptane 2:3 to 1:1, to afford the product as an off-white solid (72 mg).

後処理

  1. temperatureto cool to room temperature
  2. concentrationconcentrated in vacuo
  3. customThe residue was partitioned between aqueous sodium carbonate solution (20 ml) and ethyl acetate (20 ml)
  4. dry with materialthe organic layer dried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography
  7. washeluting with ethyl acetate:heptane 2:3 to 1:1

出典と根拠

ORDレコード
ord-77967d77034746c58e84c6a0fdda7bf8
出典データセット
uspto-grants-2009_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07572797B2

反応ノート

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