Sodium hydride → 5-Methoxy-9-(4-methoxy-benzyloxy)-7-(4-trifluoromethyl-benzyl)-6,7-dihydro-pyrrolo[3,4-g]quinolin-8-one

온도

0 °C

5-Methoxy-9-(4-methoxy-benzyloxy)-6,7-dihydro-pyrrolo[3,4-g]quinolin-8-one 304 (25.4 mg, 0.073 mmol,) was dissolved in dimethylformamide (0.4 ml) and cooled to 0° C. Sodium hydride (3.6 mg, 0.095 mmol) was added, followed by stirring at 0° C. for 5 minutes. 4-trifluoromethyl-benzylbromide (21.0 mg, 0.088 mmol) was added and the reaction mixture was allowed to warm to room temperature and kept at room temperature with stirring for 5 minutes. It was cooled to 0° C., quenched with acetic acid (0.030 ml), and concentrated in vacuo. The mixture was diluted with ethyl acetate, washed twice with water, once with brine, dried over magnesium sulfate, and concentrate in vacuo. The residue was purified by silica gel chromatography (99/1—ethyl acetate/acetic acid) to afford 5-Methoxy-9-(4-methoxy-benzyloxy)-7-(4-trifluoromethyl-benzyl)-6,7-dihydro-pyrrolo[3,4-g]quinolin-8-one 305 (13 mg, 0.026 mmol, 35%). 1H NMR δ 9.15 (dd, 1H), 8.60 (dd, 1H), 7.60 (m, 4H), 7.40 (d, 2H), 6.80 (d, 2H), 5.85 (s, 2H), 4.80 (s, 2H), 4.42 (s, 2H), 3.98 (s, 3H), 3.86 (s, 3H). MS: 509.2 (M+1).

1. temperatureto warm to room temperature
2. customkept at room temperature
3. stirringwith stirring for 5 minutes
4. temperatureIt was cooled to 0° C.
5. customquenched with acetic acid (0.030 ml)
6. concentrationconcentrated in vacuo
7. additionThe mixture was diluted with ethyl acetate
8. washwashed twice with water, once with brine
9. dry with materialdried over magnesium sulfate
10. concentrationconcentrate in vacuo
11. customThe residue was purified by silica gel chromatography (99/1—ethyl acetate/acetic acid)

ORD 기록

ord-54907bb03184466aa5fdde6543333549

출처 데이터셋

uspto-grants-2007_08

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07253180B2