2,3-Dihydro-1,4-benzothiazine → N-{[2-(2,3-dihydro-4H-1,4-benzothiazin-4-yl)pyridine-3-yl]methyl}-N-pyridin-3-ylpyridin-3-amine

Participants

Reaction Steps

To a solution of N-[(2-chloropyridin-3-yl)methyl]-N-pyridin-3-ylpyridin-3-amine (110 mg, 0.37 mmol) and 3,4-dihydro-2H-1,4-benzothiazine (85 mg, 0.56 mmol) (prepared according to procedure described in patent WO 0220498) in dry dioxane (1.25 mnL) was added sodium t-butoxide (48 mg, 0.50 mmol), and bis(tri-t-butylphosphine) palladium(0) (34 mg, 0.066 mmol). The vessel was sealed with a septum cap, degassed (3×), and heated at 100 C for 3 hours. The cooled reaction was diluted with methylene chloride and washed with NaHCO3 solution, and water and the organic layer was dried over anhydrous sodium sulfate, filtered, and the solvent evaporated. The residue was subjected to silica gel chromatography eluting with a 20-90% acetone/hexane gradient to give the title compound as a colorless glass(114 mg, 75% yield). 1H-NMR (500 MHz, CDCl3): δ 8.41 (1H, d, J=4.9 Hz), 8.28 (2H, d, J=3.7 Hz), 8.23 (2H, d, J=4.6 Hz), 7.70 (1H, d, J=6.1 Hz), 7.21-7.26 (4H, m), 7.17 (1H, d, J=3.7 Hz), 7.16 (1H, d, J=4.6 Hz), 7.06 (1H, dd, J=4.9, 7.6 Hz), 6.91 (1H, t, J=7.8 Hz), 6.84 (1H, t, J=7.6 Hz), 6.32 (1H, d, J=8.0 Hz), 4.56 (2H,s), 4.13 (2H, br s), 3.32 (2H, t, J=5.6 Hz). m/e (m+1): 412.2.

Provenance & Evidence