反应详情

At ambient temperature, to a stirred solution of 4-(9-bromo-2,3-dimethyl-naphtho[2,3-b]thiophen-4-yl)-2-cyclopentyl-phenol (0.308 g, 0.683 mmol) in N,N-DMF (3.41 mL) was added in one portion 60% NaH/mineral oil (27.3 mg, 0.683 mmol). After 0.5 h, to the reaction was added a solution of commercial 3-methoxy-4-(methoxycarbonyl)thiophene-2-sulphonylchloride (0.204 g, 0.751 mmol) in N,N-DMF (1.37 mL). After 1 h, the reaction was quenched with 1 N HCl (50 mL) combined with product from an identical experiment and extracted with 25% CH2Cl2 /EtOAc. The combined organic extracts were washed with brine (3×), dried (MgSO4) and concentrated. Purification on Biotage KP-Sil eluting with 15% EtOAc/pet. ether gave 0.593 g, (64%) of the title compound as a colorless solid. 1H NMR (DMSO-d6) δ 1.20-1.41 (m, 2 H), 1.43-1.83 (m, 9H), 2.44 (s, 3 H), 3.24 (quintet, 1 H), 3.85 (s, 3 H), 3.99 (s, 3 H), 7.24-7.38 (m, 4 H), 7.50 (t, 1 H), 7.66 (t, 1 H), 8.21 (d, 1 H), 8.81 (s, 1 H).

1. waitAfter 1 h
2. customthe reaction was quenched with 1 N HCl (50 mL)
3. extractionextracted with 25% CH2Cl2 /EtOAc
4. washThe combined organic extracts were washed with brine (3×)
5. dry with materialdried (MgSO4)
6. concentrationconcentrated
7. customPurification on Biotage KP-Sil
8. washeluting with 15% EtOAc/pet. ether