Tetrahydrofuran → 1-(Chloromethyl)-3-[(5-methoxyindol-2-yl)carbonyl]-5-hydroxy-2,3-dihydro-1H-pyrrolo[3,2-f]quinoline

Participants

Reaction Conditions

Reaction Steps

THF (6 mL) then HCO2NH4 (0.14 g, 2.21 mmol) in H2O (0.7 mL) were added to cooled (0° C.) mixture of 17d (0.11 g, 0.22 mmol) and 10% Pd/C (0.05 g) under N2. The mixture was stirred at 0° C. for 5 h, and was then filtered through Celite. The Celite was washed with CH2Cl2/H2O. The aqueous layer was extracted with CH2Cl2 (×3). The CH2Cl2 extracts were dried (brine, Na2SO4) and CH2Cl2 evaporated. Precipitation from CH2Cl2/MeOH gave 18d (0.077 g, 89%) as a grey solid: mp 224–227° C.; 1H NMR [(CD3)2SO]δ 11.66 (s, 1 H), 10.02 (bs, 1 H), 8.77 (dd, J=4.1, 1.3, 1 H), 8.41 (dd, J=8.4, 1.4, 1 H), 8.07 (s, 1 H), 7.57 (dd, J=8.4, 4.1, 1 H), 7.40 (d, J=9.0, 1 H), 7.16 (d, J=2.4, 1 H), 7.12 (d, J=1.6, 1 H), 6.92 (dd, J=8.9, 2.3, 1 H), 4.82 (dd, J=10.8, 9.4, 1 H), 4.57 (dd, J=11.0, 2.3, 1 H), 4.30 (m, 1 H), 4.04 (dd, J=11.1, 3.3, 1 H), 3.91 (dd; J=11.1, 7.2, 1 H), 3.78 (s, 3 H).

Provenance & Evidence