N-(4-Bromobutyl)phthalimide → Methyl 2-(2-bromo-5-(1-(4-(1,3-dioxoisoindolin-2-yl)butyl)-2-phenyl-1H-indole-6-carbonyl)-thiophene-3-yl)acetate

Participants

Reaction Steps

To a stirred solution of 4 (45 mg, 0.10 mmol) in anhydrous CH3CN (5 mL) was added CsF-Celite (125 mg) under N2, followed by addition of N-(4-bromobutyl)-phthalimide (28 mg, 0.10 mmol). The resulting mixture was refluxed for five hours, cooled to room temperature, and filtered. The filtrate was evaporated in vacuo. MPLC purification (Hex:EtOAc/4:1) of the residue gave 5 as a yellow solid (28 mg, 43%). 1H NMR (400 MHz, CDCl3) δ 7.98 (s, 1H), 7.74 (m, 6H), 7.59 (s, 1H), 7.47 (m, 5H), 6.60 (s, 1H), 4.32 (t, J=7.2 Hz, 2H), 3.73 (s, 3H), 3.71 (s, 2H), 3.52 (t, J=6.8 Hz, 2H), 1.72 (m, 2H), and 1.51 (m, 2H); 13C NMR (100 MHz, CDCl3) δ 187.3, 170.4, 168.5, 145.2, 144.3, 136.8, 135.6, 134.9, 134.2, 134.1, 132.5, 132.1, 130.7, 129.5, 129.0, 128.8, 123.5, 123.4, 121.5, 120.6, 112.5, 103.1, 52.5, 43.7, 37.3, 35.1, 27.4, and 25.8.

Provenance & Evidence