反应详情

745 mg (2.60 mmol) of the title B compound in Example 9, 2-(2,4-dimethoxybenzyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one, 328 mg (1.73 mmol) of the title E compound, (4-methoxyquinoline-7-yl)-methanol and 448 mg (526 mg., 2.60 mmol) of tributylphosphine are stirred in 5 mL of THF. 448 mg (2.60 mmols) of TMAD is added and the mixture is stirred for 18 h. A spatula tip of Raney nickel is added, the mixture is stirred for 10 min, and then filtered through Celite. The filtrate is evaporated to dryness and chromatographed on a Biotage 40M column with 98:2 EtOAc/EtOH to afford 2-(2,4-dimethoxy-benzyl)-5-(4-methoxy-quinolin-7-ylmethyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one: mp=128-132° C.; 1H-NMR (CDCl3) δ 3.79 (2H, s), 3.81 (3H, s), 3.85 (3H, s), 4.06 (3H, s), 4.51 (2H, s), 4.82 (2H, s), 6.46 (2H, m), 6.78 (1H, d, J=5.2) 7.30 (1H, m), 7.53 (1H, dd, J=8.5, 1.5), 7.96 (1H, s), 8.22 (1H, d J=8.5), 8.77 (1H, d, J=5.2); [M+1]+=458.

1. stirringthe mixture is stirred for 10 min
2. filtrationfiltered through Celite
3. customThe filtrate is evaporated to dryness
4. customchromatographed on a Biotage 40M column with 98:2 EtOAc/EtOH