反応式
[Br:1][C:2]1[CH:3]=[C:4]2[C@@:15]3([CH2:19][O:18][C:17]([NH2:20])=[N:16]3)[C:14]3[CH:13]=[C:12]([Cl:21])[N:11]=[C:10](F)[C:9]=3[O:8][C:5]2=[CH:6][CH:7]=1.[CH3:23][O-:24].[Na+]>CO>[Br:1][C:2]1[CH:3]=[C:4]2[C@@:15]3([CH2:19][O:18][C:17]([NH2:20])=[N:16]3)[C:14]3[CH:13]=[C:12]([Cl:21])[N:11]=[C:10]([O:24][CH3:23])[C:9]=3[O:8][C:5]2=[CH:6][CH:7]=1参加物
反応条件
- 温度
- 65 °C
実験手順
A 100 mL RBF containing a solution of (S)-7-bromo-3-chloro-1-fluoro-5′H-spiro[chromeno[2,3-c]pyridine-5,4′-oxazol]-2′-amine (0.50 g, 1.30 mmol, prepared as described in Method BB33) in methanol (13 mL) was treated with sodium methoxide (0.36 mL, 6.50 mmol) and the resulting suspension was heated to 65° C. for 3 h on a hot-plate. The reaction was cooled to RT and concentrated to dryness under high vacuum. The resulting yellowish residue was taken up in dichloromethane (75 mL), water (25 mL), and the organic layer was separated. The organic layer was dried over sodium sulfate and concentrated to yield the crude product. The crude product was purified by silica gel flash column chromatography and eluted using DCM/MeOH gradient to provide (S)-7-bromo-3-chloro-1-methoxy-5′H-spiro[chromeno[2,3-c]pyridine-5,4′-oxazol]-2′-amine as an amorphous off-white solid. [MS: m/z=395.9 (M+H)].
後処理
- temperatureThe reaction was cooled to RT
- concentrationconcentrated to dryness under high vacuum
- customwater (25 mL), and the organic layer was separated
- dry with materialThe organic layer was dried over sodium sulfate
- concentrationconcentrated
- customto yield the crude product
- customThe crude product was purified by silica gel flash column chromatography
- washeluted
出典と根拠
- ORDレコード
- ord-8962f13fae884e4ab242f69370a5f216
- 出典データセット
- uspto-grants-2014_11
- 特許番号
- US08883782B2
関連ノート
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