Dimethyl malonate → dimethyl 2-((1-(4-fluorophenyl)-1H-indazol-5-yl)methylene)malonate

反応式

[C:1]([O:8][CH3:9])(=[O:7])[CH2:2][C:3]([O:5][CH3:6])=[O:4].[F:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]2[C:25]3[C:20](=[CH:21][C:22]([CH:26]=O)=[CH:23][CH:24]=3)[CH:19]=[N:18]2)=[CH:13][CH:12]=1>C1C=CC=CC=1.C(O)(=O)C>[F:10][C:11]1[CH:12]=[CH:13][C:14]([N:17]2[C:25]3[C:20](=[CH:21][C:22]([CH:26]=[C:2]([C:1]([O:8][CH3:9])=[O:7])[C:3]([O:5][CH3:6])=[O:4])=[CH:23][CH:24]=3)[CH:19]=[N:18]2)=[CH:15][CH:16]=1

参加物

実験手順

To solution of dimethyl malonate (0.22 mL, 1.65 mmol) in benzene (15 mL) and acetic acid (3 drops) was added 1-(4-fluorophenyl)-1H-indazol-5-carboxaldehyde (330 mg, 1.38 mmol). The reaction mixture was heated at reflux overnight. The reaction was quenched with sat. KH2PO4 and extracted with EtOAc×3. The organic layers were dried over MgSO4, filtered, and concentrated. The residue was purified on SiO2 by MPLC using a 1:9 to 1:3 EtOAc/hexane gradient. Obtained 424 mg (87% yield) of dimethyl 2-((1-(4-fluorophenyl)-1H-indazol-5-yl)methylene)malonate. MS found: (M+H)+=355.