Nitrogen → HCID 59441842, compound

Participants

Reaction Conditions

Reaction Steps

To a N2 degassed solution of methyl 2-bromo-6-({2-{[4-[4-(1-methylethyl)-1-piperazinyl]-2-(methyloxy)phenyl]amino}-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}amino)benzoate (500 mg, 0.668 mmol) in N,N-Dimethylformamide (DMF) (10 ml) was added tetrakis(triphenylphosphine)palladium(0) (154 mg, 0.134 mmol) and zinc cyanide (94 mg, 0.801 mmol). The reaction was heated in the microwave at 120° C. for 10 min. The solvent was then removed, the residue redissolved in DCM (50 ml), washed with water (50 ml), adsorbed onto silica gel, and purified by silica gel chromatography (DCM to 5% MeOH/DCM) to afford methyl 2-cyano-6-({2-{[4-[4-(1-methylethyl)-1-piperazinyl]-2-(methyloxy)phenyl]amino}-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}amino)benzoate (0.4 g, 86%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.01 (d, J=6.62 Hz, 6 H) 2.33 (s, 3 H) 2.57-2.64 (m, 4 H) 2.65-2.72 (m, 1 H) 3.09-3.18 (m, 4 H) 3.63 (s, 3 H) 3.83 (s, 3 H) 6.53-55 (m, 1 H) 6.64-6.66 (m, 1 H) 6.81 (d, J=4.01 Hz, 1 H) 7.36 (d, J=8.03 Hz, 2 H) 7.38 (d, J=4.01 Hz, 1 H) 7.52-7.57 (m, 1 H) 7.58-7.65 (m, 1 H) 7.71-7.74 (m, 1 H) 7.91 (d, J=8.23 Hz, 2 H) 7.95 (s, 1 H) 7.99-8.04 (m, 1 H) 9.95 (s, 1 H).

Provenance & Evidence