Potassium Phosphate, Tribasic → (S)-5-amino-2'-(5,6-dihydro-2H-pyran-3-yl)-4'-fluoro-2,6-dihydrospiro[[1,4]oxazine-3,9'-xanthen]-7'-ol
反応式
P([O-])([O-])([O-])=O.[K+].[K+].[K+].[NH2:9][C:10]1[CH2:31][O:30][CH2:29][C@:12]2([C:25]3[CH:24]=[C:23](Br)[CH:22]=[C:21]([F:27])[C:20]=3[O:19][C:18]3[C:13]2=[CH:14][C:15]([OH:28])=[CH:16][CH:17]=3)[N:11]=1.[O:32]1[CH2:37][CH2:36][CH:35]=[C:34](B2OC(C)(C)C(C)(C)O2)[CH2:33]1>O1CCOCC1.O.CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C.CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C.Cl[Pd]Cl>[NH2:9][C:10]1[CH2:31][O:30][CH2:29][C@:12]2([C:25]3[CH:24]=[C:23]([C:34]4[CH2:33][O:32][CH2:37][CH2:36][CH:35]=4)[CH:22]=[C:21]([F:27])[C:20]=3[O:19][C:18]3[C:13]2=[CH:14][C:15]([OH:28])=[CH:16][CH:17]=3)[N:11]=1参加物
反応物 3
生成物 1
試薬・触媒・溶媒 3
反応条件
- 温度
- 120 °C
実験手順
In a microwave vial, the potassium phosphate (1.014 g, 4.78 mmol), PdCl2(AmPhos)2 (0.085 g, 0.119 mmol), (S)-5-amino-2′-bromo-4′-fluoro-2,6-dihydrospiro[[1,4]oxazine-3,9′-xanthen]-7′-ol (0.604 g, 1.593 mmol), and 2-(5,6-dihydro-2H-pyran-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.485 g, 2.310 mmol) were suspended in dioxane (6.5 mL) and water (2.5 mL). Argon gas was blown through the vessel, which was sealed and heated by microwave at 120° C. for 30 min. The mixture was concentrated. The residue was neutralized with half-saturated aqueous NH4Cl (35 mL). The aqueous phase was extracted with 5% MeOH/DCM (3×35 mL). The organics were combined, washed with dilute brine (15 mL), dried over sodium sulfate and concentrated to afford crude (S)-5-amino-2′-(5,6-dihydro-2H-pyran-3-yl)-4′-fluoro-2,6-dihydrospiro[[1,4]oxazine-3,9′-xanthen]-7′-ol which was used directly in the next step.
後処理
- customwas sealed
- concentrationThe mixture was concentrated
- extractionThe aqueous phase was extracted with 5% MeOH/DCM (3×35 mL)
- washwashed with dilute brine (15 mL)
- dry with materialdried over sodium sulfate
- concentrationconcentrated
出典と根拠
- ORDレコード
- ord-180d19445e584931af9663249e61bf5c
- 出典データセット
- uspto-grants-2013_07
- 特許番号
- US08497264B2
反応ノート
読み込み中…