Cesium carbonate → N-benzyl-5-phenyl-2-vinylpyrrolo[2,1-f][1,2,4]triazin-4-amine

Participants

Reaction Conditions

Reaction Steps

N-Benzyl-2-chloro-5-phenylpyrrolo[2,1-f][1,2,4]triazin-4-amine (0.300 g, 0.896 mmol) (as in Example 4) and 2,4,6-trivinyl cyclotriboroxane pyridine complex (0.323 g, 1.34 mmol) were dissolved in dioxane (15 mL) and then cesium carbonate (0.584 g, 1.79 mmol) dissolved in water (2 mL) was added. The reaction mixture was degassed with nitrogen for 15 minutes, then tetrakistriphenylphosphine palladium (0.0520 g, 0.0450 mmol) was added and the resulting reaction mixture degassed for 15 minutes. The reaction mixture was then heated to 110° C. for 14 h, allowed to cool, concentrated under reduced pressure and CH2Cl2 (25 mL) was added. The residue was filtered through a CELITE® bed and the filterate dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography using CombiFlash (REDISEP®, silica gel, 24 g, 3% methanol in chloroform) to yield N-benzyl-5-phenyl-2-vinylpyrrolo[2,1-f][1,2,4]triazin-4-amine (0.200 g, 34.2%). LCMS Condition B-25: retention time 3.12 min, [M+1]=327.2. 1H NMR (400 MHz, DMSO-d6) δ ppm 4.72 (d, J=5.6 Hz, 2H), 5.60 (d, J=2.4 Hz, J=10.4 Hz, 1H), 6.36-6.56 (m, 3H), 6.72 (d, J=2.8 Hz, 1H), 7.30-7.37 (m, 5H), 7.42-7.52 (m, 5H), 7.74 (d, J=2.8 Hz, 1H).

Provenance & Evidence