反応式
[C@@H:1]12[CH2:7][NH:6][C@@H:5]1[CH2:4][N:3]([C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])[CH2:2]2.C([O-])([O-])=O.[Cs+].[Cs+].Br[C:25]1[CH:26]=[N:27][CH:28]=[C:29]([C:31]#[N:32])[CH:30]=1>C1(C)C=CC=CC=1.C(OCC)(=O)C.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].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>[C:31]([C:29]1[CH:30]=[C:25]([N:6]2[CH2:7][C@@H:1]3[C@H:5]2[CH2:4][N:3]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:2]3)[CH:26]=[N:27][CH:28]=1)#[N:32]参加物
反応物 3
生成物 1
試薬・触媒・溶媒 4
反応条件
- 温度
- 100 °C
実験手順
The product of Example 52D (830 mg, 3.58 mmol) in toluene (20 mL) was treated with Pd2(dba)3 (71.0 mg, 0.072 mmol), BINAP (134 mg, 0.214 mmol), Cs2CO3 (2.32 g, 7.16 mmol) and 3-bromo-5-cyanopyridine (0.98 g, 5.37 mmol). The mixture was heated at 100° C. under N2 for 10 hours and then allowed to cool to room temperature and diluted with ethyl acetate (100 mL). The brown solution was washed with water (2×10 mL) and concentrated under reduced pressure. The residue was purified by chromatography (SiO2, EtOAc:hexane, 50:50, Rf 0.3) to provide the title compound (770 mg, 64% yield). 1H NMR (MeOH-d4, 300 MHz) δ 3.2(dd, J=12.9, 4. Hz, 1H), 3.30-3.4 (m, 2H), 3.6 (dd, J=8.2, 3. Hz, 1H), 3.96-4.10 (m, 3H), 4.74 (dd, J=6.1, 4.0 Hz, 1H), 5.10 (m, 2H), 7.15 (dd, J=2.7, 1.7 Hz, 1H), 7.25 (m, 3H), 7.35 (m, 2H), 7.96 (d, J=2.7 Hz, 1H), 8.15 (d, J=1.7 Hz, 1H); MS (DCI/NH3) m/z 335 (M+H)+.
後処理
- temperatureto cool to room temperature
- washThe brown solution was washed with water (2×10 mL)
- concentrationconcentrated under reduced pressure
- customThe residue was purified by chromatography (SiO2, EtOAc:hexane, 50:50, Rf 0.3)
出典と根拠
- ORDレコード
- ord-eb4cc527aa66444ba1dd5a9754e18eea
- 出典データセット
- uspto-grants-2012_02
- 特許番号
- US08119635B2
関連ノート
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