Dimethylformamide → HCID 68264841, compound

Reaction equation

[Cl:1][C:2]1[C:10]2[NH:9][C:8]3[C:11](=[O:14])[CH2:12][CH2:13][C:7]=3[C:6]=2[CH:5]=[C:4]([Cl:15])[CH:3]=1.[C:16]([O-:19])([O-])=O.[K+].[K+].CN([CH:25]=[O:26])C>O>[C:16]([O:26][CH2:25][N:9]1[C:10]2[C:2]([Cl:1])=[CH:3][C:4]([Cl:15])=[CH:5][C:6]=2[C:7]2[CH2:13][CH2:12][C:11](=[O:14])[C:8]1=2)(=[O:19])[C:6]([CH3:7])([CH3:10])[CH3:5]

Participants

Procedure

To a solution of 5,7-dichloro-1,2-dihydrocyclopenta[b]indol-3(4H)-one (0.1 g, 0.41 mmol) in anhydrous DMF (5 mL), K2CO3 (80 mg, 0.62 mmol) was added followed by chloro methyl pivalate (0.07 mL, 0.51 mmol) and the resulting mixture stirred at room temperature for 3 h. The reaction mixture was diluted with water (10 mL) and extracted with EtOAc (3×10 mL). The combined organic extracts were dried over Na2SO4 and concentrated under reduced pressure to give the crude compound which was purified by silica gel chromatography [EtOAc-hexane (3:17) as eluant] to provide the title compound as a yellow solid (0.10 g, 68%). 1H NMR (500 MHz, CDCl3, δ in ppm) 7.61 (s, 1H), 7.41 (s, 1H), 6.56 (s, 2H), 3.04 (s, 4H), 1.14 (s, 9H).