Morpholine → HCID 50994270, compound

Participants

Reaction Steps

To (2-chloro-pyridin-4-yl)-(3,5-dibromo-phenyl)-methanone (0.200 g, 0.53 mmol) in 1.0 mL of 1,4-dioxane in a microwave tube was added 0.070 g (0.80 mmol) morpholine. The reaction was subjected to microwave irradiation at 120° C. for 60 minutes. The reaction mixture was cooled and concentrated. The crude product was chromatographed on silica gel using 1:1 hexane:ethyl acetate to give 0.118 g of the (3,5-dibromo-phenyl)-(2-morpholin-4-yl-pyridin-4-yl)-methanone. This compound was converted to [3-(1H-indol-4-yl)-5-(2-morpholin-4-yl-pyridine-4-carbonyl)-phenyl]-carbamic acid methyl ester as described for Example 90. 1H NMR (400 MHz, CDCl3): δ 8.28 (d, J=5.3 Hz, 1H), 8.07 (t, J=1.8 Hz, 1H), 7.95 (s, 1H), 7.76 (t, J=1.6 Hz, 1H), 7.41 (d, J=8.2 Hz, 1H), 7.29 (d, J=3.3 Hz, 1H), 7.18 (t, J=7.7 Hz, 1H), 7.10 (d, J=7.4 Hz, 1H), 7.08 (s, 1H), 6.95 (dd, J=5.1, 1.0 Hz, 1H), 6.62 (d, J=3.1 Hz, 1H), 3.78 (t, J=4.9 Hz, 4H), 3.75 (s, 3H), 3.54 (t, J=4.9 Hz, 4H).

Provenance & Evidence