反応式
Br[C:2]1[C:8]([F:9])=[CH:7][C:6]([N+:10]([O-:12])=[O:11])=[CH:5][C:3]=1[NH2:4].B1([CH:24]2[CH2:26][CH2:25]2)OC(=O)CN(C)CC(=O)O1.P(C1CCCCC1)(C1CCCCC1)C1CCCCC1.C([O-])([O-])=O.[Cs+].[Cs+]>C1(C)C=CC=CC=1.O.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH:24]1([C:2]2[C:8]([F:9])=[CH:7][C:6]([N+:10]([O-:12])=[O:11])=[CH:5][C:3]=2[NH2:4])[CH2:26][CH2:25]1参加物
反応物 4
生成物 1
試薬・触媒・溶媒 3
反応条件
- 温度
- 100 °C
実験手順
A mixture of 2-bromo-3-fluoro-5-nitroaniline (1.6 g, 6.81 mmol, 1 equiv), cyclopropylboronic acid MIDA ester (Aldrich; 4.0 g, 20.43 mmol, 3 equiv), Pd(OAc)2 (238 mg, 1.06 mmol, 0.15 equiv), Cy3P (578 mg, 2.06 mmol, 0.3 equiv) and Cs2CO3 (13.26 g, 40.8 mmol, 6 equiv) in toluene (70 mL) and H2O (14 mL) was de-gassed with N2 for 5 minutes. The mixture was then heated at 100° C. (oil bath temperature) overnight. After allowing to cool to room temperature, the mixture was diluted with EtOAc (100 mL) and H2O (50 mL) and the mixture filtered through Celite. The filter cake was washed with EtOAc (2×50 mL) and the filtrate partitioned. The organic layer was evaporated under vacuum to leave a crude residue which was purified by column chromatography on silica gel using EtOAc/hexanes (1:4) as eluent to give the product (1.2 g, 90%) as a dark yellow solid.
後処理
- customwas de-gassed with N2 for 5 minutes
- temperatureto cool to room temperature
- additionthe mixture was diluted with EtOAc (100 mL) and H2O (50 mL)
- filtrationthe mixture filtered through Celite
- washThe filter cake was washed with EtOAc (2×50 mL)
- customthe filtrate partitioned
- customThe organic layer was evaporated under vacuum
- customto leave a crude residue which
- customwas purified by column chromatography on silica gel
出典と根拠
- ORDレコード
- ord-e929fd94b6cd4f05be589ba0d3fc485c
- 出典データセット
- uspto-grants-2015_11
- 特許番号
- US09181222B2
関連ノート
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