反応式
C(=O)([O-])O.[Na+].Cl[C:7]1[N:8]=[CH:9][C:10]([C:13]([O:15]C)=[O:14])=[N:11][CH:12]=1.CC1(C)C(C)(C)OB([C:25]2[CH2:26][CH2:27][N:28]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:29][CH:30]=2)O1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>COCCOC.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:37][C:34]([O:33][C:31]([N:28]1[CH2:27][CH:26]=[C:25]([C:7]2[N:8]=[CH:9][C:10]([C:13]([OH:15])=[O:14])=[N:11][CH:12]=2)[CH2:30][CH2:29]1)=[O:32])([CH3:35])[CH3:36]参加物
反応物 4
生成物 1
試薬・触媒・溶媒 3
反応条件
- 温度
- 80 °C
実験手順
Saturated aqueous sodium hydrogen carbonate solution (5.00 ml) was added to methyl 5-chloropyrazine-2-carboxylate (173 mg, 1.00 mmol), tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylate (371 mg, 1.20 mmol), palladium(II) acetate (11 mg, 0.05 mmol) and triphenylphosphine (52 mg, 0.20 mmol) in 1,2-dimethoxyethane (5.00 ml) at 25° C. under nitrogen. The resulting mixture was stirred at 80° C. for 4 h. The reaction mixture was diluted with water (50 mL) and washed with EtOAc (50 mL). The aqueous layer was adjusted to pH 1 using HCl (2M aqueous solution) and extracted with EtOAc (2×50 mL). The combined organics were dried over MgSO4 and concentrated under reduced pressure to afford 5-[1-[(2-methylpropan-2-yl)oxycarbonyl]-3,6-dihydro-2H -pyridin-4-yl]pyrazine-2-carboxylic acid (305 mg, 100%) as a yellow solid. This was used directly in the next reaction, with no further purification.
後処理
- washwashed with EtOAc (50 mL)
- extractionextracted with EtOAc (2×50 mL)
- dry with materialThe combined organics were dried over MgSO4
- concentrationconcentrated under reduced pressure
出典と根拠
- ORDレコード
- ord-269a3bc3f85641879f7f11c992bfec72
- 出典データセット
- uspto-grants-2010_06
- 特許番号
- US07737149B2
関連ノート
読み込み中…