Ethanol → Ethyl 1-(2,6-difluorophenyl)-6-oxo-6,7-dihydro-1H-pyrazolo[3,4-b]pyridine-5-carboxylate
反応式
[NH2:1][C:2]1[N:6]([C:7]2[C:12]([F:13])=[CH:11][CH:10]=[CH:9][C:8]=2[F:14])[N:5]=[CH:4][C:3]=1[CH:15]=O.NC1N(C2C=CC=CC=2Cl)N=CC=1C=O.C(O)C.[C:35](OCC)(=[O:42])[CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38].N1CCCCC1>>[F:13][C:12]1[CH:11]=[CH:10][CH:9]=[C:8]([F:14])[C:7]=1[N:6]1[C:2]2[NH:1][C:35](=[O:42])[C:36]([C:37]([O:39][CH2:40][CH3:41])=[O:38])=[CH:15][C:3]=2[CH:4]=[N:5]1参加物
反応物 5
生成物 1
反応条件
- 温度
- 75 °C
実験手順
In a 500 mL round-bottomed flask was added 5-amino-1-(2,6-difluorophenyl)-1H-pyrazole-4-carbaldehyde (7.77 g, 35 mmol; prepared in a fashion similar to that described for 5-amino-1-(2-chlorophenyl)-1H-pyrazole-4-carbaldehyde in Example 1 above) followed by ethanol (100 ml, 35 mmol). To the solution was added diethyl malonate (11 ml, 70 mmol) and piperidine (3.4 ml, 35 mmol) and the mixture was heated to 75° C. overnight. The reaction mixture was concentrated under reduced pressure and the brown residue was treated with 200 mL of a 1:1 solution of EtOAc:Hexanes. The precipitated solid was then filtered through a sintered glass frit and rinsed with hexanes. It was dried under high vacuum to afford the title compound (11.13 g, 100% yield) as a beige crystalline solid. MS (ESI, pos.ion) m/z: 306.0 (M+1).
後処理
- customprepared in a fashion similar to
- concentrationThe reaction mixture was concentrated under reduced pressure
- additionthe brown residue was treated with 200 mL of a 1:1 solution of EtOAc
- filtrationThe precipitated solid was then filtered through a sintered glass frit
- washrinsed with hexanes
- customIt was dried under high vacuum
出典と根拠
- ORDレコード
- ord-a312d8c5dacb48bcb12f4c562cf1a98f
- 出典データセット
- uspto-grants-2011_09
- 特許番号
- US08022085B2
反応ノート
読み込み中…