反応式
[CH:1]([C:3]1[C:4]([C:24]([F:27])([F:26])[F:25])=[N:5][N:6]([CH2:8][C:9]([NH:11][C:12]2[S:16][C:15]3[CH2:17][CH2:18][CH2:19][CH2:20][C:14]=3[C:13]=2[C:21]([NH2:23])=[O:22])=[O:10])[CH:7]=1)=[O:2].[CH3:28][Mg]Br.C(OCC)C>C1COCC1>[OH:2][CH:1]([C:3]1[C:4]([C:24]([F:27])([F:25])[F:26])=[N:5][N:6]([CH2:8][C:9]([NH:11][C:12]2[S:16][C:15]3[CH2:17][CH2:18][CH2:19][CH2:20][C:14]=3[C:13]=2[C:21]([NH2:23])=[O:22])=[O:10])[CH:7]=1)[CH3:28]参加物
反応物 3
生成物 1
試薬・触媒・溶媒 1
反応条件
- 温度
- -50 °C
実験手順
To 2-(2-(4-formyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetamido)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide (1.6 g, 4.00 mmol) in THF (10 mL) at −50° C. under an argon atmosphere was added 3M methylmagnesium bromide in diethyl ether (1.249 mL, 3.75 mmol) in a dropwise manner over 10 min. The reaction was stirred at −50° C. for 1.5 h. The reaction was quenched with saturated aqueous NH4Cl before partitioning between EtOAc/water (×2), and washing with EtOAc (×1) and brine (×1). The organics were dried over MgSO4 before removing the solvent in vacuo. The residue was purified by silica gel flash chromatography (1:2 heptane/EtOAc) and the solvent removed in vacuo to give the title compound as a yellow solid (0.8 g, 1.921 mmol, 48%).
後処理
- customThe reaction was quenched with saturated aqueous NH4Cl
- custombefore partitioning between EtOAc/water (×2)
- washwashing with EtOAc (×1) and brine (×1)
- dry with materialThe organics were dried over MgSO4
- custombefore removing the solvent in vacuo
- customThe residue was purified by silica gel flash chromatography (1:2 heptane/EtOAc)
- customthe solvent removed in vacuo
出典と根拠
- ORDレコード
- ord-d087b1b55b21408896cc5cfe9643e8d9
- 出典データセット
- uspto-grants-2010_10
- 特許番号
- US07820707B2
関連ノート
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