反応式
[OH:1][C:2]1[CH:3]=[C:4]([O:15][C:16]2[CH:17]=[N:18][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:20][CH:21]=2)[CH:5]=[C:6]2[C:10]=1[NH:9][C:8]([C:11]([O:13][CH3:14])=[O:12])=[CH:7]2.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.[CH3:57][O:58][CH2:59][CH:60](O)[CH2:61][O:62][CH3:63]>O1CCCC1>[CH3:57][O:58][CH2:59][CH:60]([CH2:61][O:62][CH3:63])[O:1][C:2]1[CH:3]=[C:4]([O:15][C:16]2[CH:17]=[N:18][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:20][CH:21]=2)[CH:5]=[C:6]2[C:10]=1[NH:9][C:8]([C:11]([O:13][CH3:14])=[O:12])=[CH:7]2参加物
反応物 4
生成物 1
試薬・触媒・溶媒 1
反応条件
- 温度
- 50 °C
実験手順
A mixture of methyl 7-hydroxy-5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-1H-indole-2-carboxylate (1.2 g), tributylphosphine (1.6 mL), 1,1′-(azodicarbonyl)dipiperidine (1.7 g), 1,3-dimethoxypropan-2-ol (0.8 g) and tetrahydrofuran (20 mL) was stirred at 50° C. for 13 h. Tributylphosphine (0.82 mL), 1,1′-(azodicarbonyl)dipiperidine (0.83 g) and 1,3-dimethoxypropan-2-ol (0.4 g) were added to the mixture again and the mixture was stirred at 70° C. for 5 h. Furthermore, tributylphosphine (1.64 mL), 1,1′-(azodicarbonyl)dipiperidine (1.66 g) and 1,3-dimethoxypropan-2-ol (0.8 g) were added to the mixture. After stirring at 70° C. for 3 h, the mixture was cooled to 0° C., and insoluble materials were removed by filtration. The filtrate was concentrated and the residue was purified basic silica gel column chromatography (ethyl acetate/hexane=20/80 to 85/15, volume ratio) to give the title compound (1.79 g, 84%) as an orange oil, MS 463 (MH−).
後処理
- stirringthe mixture was stirred at 70° C. for 5 h
- stirringAfter stirring at 70° C. for 3 h
- temperaturethe mixture was cooled to 0° C.
- custominsoluble materials were removed by filtration
- concentrationThe filtrate was concentrated
- customthe residue was purified basic silica gel column chromatography (ethyl acetate/hexane=20/80 to 85/15, volume ratio)
出典と根拠
- ORDレコード
- ord-a08066e159044363ac0c078d373e5c44
- 出典データセット
- uspto-grants-2014_03
- 特許番号
- US08673942B2
関連ノート
読み込み中…