Sodium Carbonate → 2-(4-isopropylsulfonylphenyl)-5H-pyrrolo[2,3-b]pyrazine

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Reaction Conditions

Reaction Steps

2-bromo-5H-pyrrolo[2,3-b]pyrazine (6.5 g, 32.82 mmol), (4-isopropylsulfonylphenyl) boronic acid (7.859 g, 34.46 mmol) and palladium triphenylphosphane complex (1.896 g, 1.641 mmol) were combined in a round bottomed flask. To this mixture was added dioxane (97.50 mL) and then an aqueous solution of Na2CO3 (49.23 mL of 2 M, 98.46 mmol). The resulting suspension was stirred at 100° C. overnight, then heating was stopped and water added. The resultant precipitate was collected and dried in vacuo at 40° C., to give the sub-title compound as a brown solid (9.45 g, 95% yield). 1H NMR (400.0 MHz, DMSO) δ 12.25 (s, 1H), 9.00 (s, 1H), 8.43 (d, J=8.4 Hz, 2H), 7.99-7.96 (m, 3H), 6.74 (d, J=3.5 Hz, 1H), 3.57 (s, 1H) and 1.20 (d, J=6.8 Hz, 6H) ppm; MS (ES+) 435.2.

Provenance & Evidence