Sodium Carbonate → HCID 58529515, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution 3-(4-amino-5-bromo-pyrrolo[2,1-f][1,2,4]triazine-7-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (1.33 g, 3.24 mmol), intermediate C (1.63 g, 4.86 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.37 g, 0.32 mmol) in degassed DMF (35 mL) was added aqueous Na2CO3 (2M, 5.34 mL). The resulting mixture was heated at 110° C. for 3 h and then cooled to rt. The reaction mixture was diluted with EtOAc and filtered through a Celite® pad. The organic layer was separated and concentrated in vacuo. The residue was purified by silica-gel column using a gradient of 50 to 100% EtOAc in hexanes to afford 1.16 g (66%) of the desired product. 1H-NMR (CD3OD-d4) 8.39 (s, 1H), 8.05 (s, 1H), 7.87 (dd, 1H), 7.70 (s, 1H), 7.50 (s, 1H), 7.37-7.29, (m, 5 H), 7.24 (dd, 1 H), 5.67 (s, 1 H), 4.47-4.39 (m, 2 H), 3.71-3.59 (m, 2 H), 2.34-2.12 (m, 2 H), 1.45 (s, 1H); LC-MS [M+H]+=537.9, RT=3.36 min.

Provenance & Evidence