Potassium Sodium Tartrate → HCID 72670105, compound

Participants

Reaction Steps

A 500-mL RBF was charged with 3-((5-amino-7-bromo-3-chloro-5H-chromeno[2,3-c]pyridin-5-yl)methoxy)propanenitrile (3.967 g, 10.05 mmol) and toluene (100 mL) to give a clear solution. Trimethylaluminum (10.55 mL of a 2M solution in toluene, 21.11 mmol) was added, and the resulting mixture was stirred for 5 min. A reflux condenser was attached, and the mixture was heated to reflux for 1 h. After the mixture had cooled to RT, a saturated aq. Rochelle's salt solution (200 mL) was slowly added. The mixture was stirred vigorously for 48 h and was then diluted with EtOAc (200 mL) and water (300 mL). The layers were separated, and the aq. layer was extracted with EtOAc (2×200 mL). The combined organic extracts were washed with water (200 mL), washed with brine, dried over sodium sulfate, filtered, and concentrated. The residue was taken up in DCM/MeOH and filtered to give 615 mg of the desired product an off-white solid. The filtrate was concentrated, and the residue was purified by chromatography on silica gel (0-10% MeOH/DCM). The product obtained from chromatography was combined with the above solid to give 7-bromo-3-chloro-6′,7′-dihydro-2′H-spiro[chromeno[2,3-c]pyridine-5,3′-[1,4]oxazepin]-5′-amine as a cream-colored solid. 1H NMR (400 MHz, DMSO-d6) δ=8.37 (d, J=0.4 Hz, 1 H), 7.62-7.43 (m, 2 H), 7.35 (s, 1 H), 7.22 (dd, J=0.5, 8.4 Hz, 1 H), 6.27 (br. s., 2 H), 3.94-3.72 (m, 2H), 3.70-3.47 (m, 2 H), 3.05-2.75 (m, 2 H). MS m/z=394.0. Calc'd for C16H14BrClN3O2: 394.0.

Provenance & Evidence