反応式
[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][CH:13]=[C:12](OS(C(F)(F)F)(=O)=O)[C:9]=2[C:10]=1[CH3:11])=[O:5])[CH3:2].[CH:24]1([C:27]([NH2:29])=[O:28])[CH2:26][CH2:25]1.C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.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]>[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][CH:13]=[C:12]([NH:29][C:27]([CH:24]3[CH2:26][CH2:25]3)=[O:28])[C:9]=2[C:10]=1[CH3:11])=[O:5])[CH3:2]参加物
反応物 4
生成物 1
試薬・触媒・溶媒 2
実験手順
To 3-methyl-4-trifluoromethanesulfonyloxy-benzofuran-2-carboxylic acid ethyl ester (300 mg, 0.85 mmol, 1 eq, prepared according to Example 20, Step 1) in 8 mL of dioxane under nitrogen were added cyclopropyl carboxamide (87 mg, 1.02 mmol, 1.2 eq), Pd2 (dba)3 (16 mg, 0.017 mmol, 0.02 eq), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (30 mg, 0.051 mmol, 0.06 eq), and cesium carbonate (390 mg, 1.19 mmol, 1.4 eq). The reaction mixture was heated at reflux for 72 h. After work up and column chromatography (dichloromethane/hexanes), 4-(cyclopropanecarbonyl-amino)-3-methyl-benzofuran-2-carboxylic acid ethyl ester was obtained in 98% yield (238 mg). 1H NMR (400 MHz, DMSO-d6) δ ppm 0.8 (m, 4 H) 1.3 (t, J=7.1 Hz, 3 H) 1.8 (s, 1 H) 2.6 (s, 3 H) 4.4 (q, J=7.2 Hz, 2 H) 7.2 (d, J=7.1 Hz, 1 H) 7.5 (m, 1 H) 7.5 (m, 1 H) 10.1 (s, 1 H).
後処理
- temperatureThe reaction mixture was heated
- temperatureat reflux for 72 h
出典と根拠
- ORDレコード
- ord-6cb6a804429c49f08029e7b531d8aa19
- 出典データセット
- uspto-grants-2008_09
- 特許番号
- US07420001B2
関連ノート
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