Benzylamine → HCID 71143763, compound

Participants

Reaction Conditions

Reaction Steps

7-iodo-2-(4-isopropylsulfonylphenyl)-5-(p-tolylsulfonyl)pyrrolo[2,3-b]pyrazine (100 mg, 0.3 mmol), benzylamine (160.7 mg, 1.5 mmol), (5-diphenylphosphanyl-9,9-dimethyl-xanthen-4-yl)-diphenyl-phosphane (9.5 mg, 0.016 mmol), palladium diacetate (3.7 mg, 0.016 mmol) and sodium carbonate (70 mg, 0.65 mmol) were added to dioxane (2 mL) in a sealed flask. The reaction was flushed well with carbon monoxide and heated to 60° C. overnight. 2M aqueous LiOH (2 mL) was added and the resultant mixture stirred overnight, then the volatile components were stripped under a stream of nitrogen gas at 60° C. and the solid residue taken up in DMSO (2 mL). This solution was filtered and then purified by FractionLynx mass directed HPLC, then freeze dried to give N-benzyl-2-(4-(isopropylsulfonyl)phenyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (8.9 mg, 15%). 1H NMR (400.0 MHz, DMSO) δ 12.94 (d, J=2.5 Hz, 1H), 9.13 (s, 1H), 8.68 (t, J=5.8 Hz, 1H), 8.54 (d, J=3.1 Hz, 1H), 8.41 (d, J=8.5 Hz, 2H), 7.94 (d, J=8.5 Hz, 2H), 7.46 (d, J=7.2 Hz, 2H), 7.41-7.37 (m, 2H), 7.30 (t, J=7.3 Hz, 1H), 7.30 (s, 1H), 4.67 (d, J=5.7 Hz, 1H), 3.51 (t, J=6.8 Hz, 1H) and 1.21 (d, J=6.9 Hz, 6H) ppm; MS (ES+) 435.2.

Provenance & Evidence