Water → 2-(2-{2-Methoxy-4-[4-(4-methyl-piperazin-1-yl)-piperidin-1-yl]-phenylamino}-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-N,N-dimethyl-benzenesulfonamide

Participants

Reaction Conditions

Reaction Steps

A mixture of (7-Bromo-pyrrolo[2,1-f][1,2,4]triazin-2-yl)-{2-methoxy-4-[4-(4-methyl-piperazin-1-yl)-piperidin-1-yl]-phenyl}-amine (0.09 g, 0.0002 mol) and N,N-dimethylsulfonamide-2-benzeneboronic acid (0.060 g, 0.00026 mol), Tetrakis(triphenylphosphine)palladium(0) (0.023 g, 0.000020 mol), 1 M of Sodium carbonate in Water (0.7 mL, 0.0007 mol), Tetrahydrofuran (4 mL,) and ethanol (4 mL) under nitrogen was heated at 80° C. overnight. Purification by prep plate chromatography gave 2-(2-{2-Methoxy-4-[4-(4-methyl-piperazin-1-yl)-piperidin-1-yl]-phenylamino}-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-N,N-dimethyl-benzenesulfonamide (0.052 g, 48%) as a tan solid. MP; 198-205° C.; 1H-NMR (DMSO-d6, 400 MHz) δ 8.91 (s, 1H), 8.04-8.02 (d, 1H, J=7.80 Hz), 7.81-7.79 (t, 1H, J=7.44 Hz), 7.77-7.75 (t, 1H, J=7.56 Hz), 7.65-7.63 (d, 1H, J=7.48 Hz), 7.53-7.51 (d, 1H, J=8.76 Hz), 7.46 (s, 1H), 6.91-6.86 (q, 1H, J=4.56 Hz), 6.58-6.57 (d, 1H, J=2.40 Hz), 6.16-6.13 (d, 1H, J=12.44 Hz), 3.80 (s, 3H), 3.60-3.56 (d, 2H, J=12.44 Hz), 2.35 (s, 6H), 2.17 (s, 3H), 1.83-1.80 (d, 2H, J=11.88 Hz), 1.49-1.46 (q, 2H, J=8.52 Hz) 1.23 (s, 1H).

Provenance & Evidence