反応式
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1.C(=O)([O-])[O-].[K+].[K+].I[C:50]1[C:55]([O:56][CH3:57])=[CH:54][CH:53]=[C:52]([CH3:58])[N:51]=1>C(#N)C.CC([O-])=O.CC([O-])=O.[Pd+2].O>[CH3:57][O:56][C:55]1[C:50]([C:6]2[CH:7]=[CH:8][C:3]([C:2]([F:13])([F:12])[F:1])=[CH:4][CH:5]=2)=[N:51][C:52]([CH3:58])=[CH:53][CH:54]=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
- 75 °C
実験手順
To a mixture of 4-(trifluoromethyl)phenylboronic acid (0.97 g, 5.1 mmol), S—PHOS (0.20 g, 0.47 mmol), potassium carbonate (2.0 g, 15 mmol), and Pd(OAc)2 (0.061 g, 0.27 mmol) was added a solution of 2-iodo-3-methoxy-6-methylpyridine (prepared in the previous step) in acetonitrile (6 mL) followed by water (4 mL). The reaction mixture was degassed by bubbling nitrogen through the solution for 10 min, and the reaction mixture was heated to 75° C. After 4 h, the reaction mixture was diluted with EtOAc, washed with saturated NaHCO3 (1×), brine (1×), dried over MgSO4, filtered, and concentrated. Purification by flash column chromatography on silica gel (5% to 20% EtOAc in hexanes) gave 3-methoxy-6-methyl-2-(4-(trifluoromethyl)phenyl)pyridine.
後処理
- customThe reaction mixture was degassed
- customby bubbling nitrogen through the solution for 10 min
- additionthe reaction mixture was diluted with EtOAc
- washwashed with saturated NaHCO3 (1×), brine (1×)
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated
- customPurification by flash column chromatography on silica gel (5% to 20% EtOAc in hexanes)
出典と根拠
- ORDレコード
- ord-0efef0adc9b44a178b643bef49bc58a1
- 出典データセット
- uspto-grants-2014_07
- 特許番号
- US08791147B2
関連ノート
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