Sodium Carbonate → 2-(4-Isopropylsulfonylphenyl)-5-trityl-pyrrolo[2,3-b]pyrazin-7-amine

Participants

Reaction Conditions

Reaction Steps

2-bromo-5-trityl-pyrrolo[2,3-b]pyrazin-7-amine (300 mg, 0.6588 mmol), (4-isopropylsulfonylphenyl)boronic acid (180.3 mg, 0.7906 mmol) and Na2CO3 (988.0 μL of 2 M, 1.976 mmol) combined in dioxane (3 mL) in a microwave tube and the mixture de-gassed (×2 vacuum-N2 cycles). Pd (tBu3P)2 (33.67 mg, 0.06588 mmol) added and the mixture de-gassed (×2 cycles) then heated at 65° C. (block temp), sealing tube with a crimp-top and left to stir for 1 hour. Reaction mixture cooled to ambient temperature and the mixture partitioned between DCM and water. Aqueous phase extracted with DCM and combined organics dried and concentrated. Residue purified by chromatography eluting with 0-30% MeOH-DCM. Brown/yellow solid obtained (332 mg, 90%). 1H NMR (400.0 MHz, DMSO) δ 8.67 (s, 1H), 8.35 (d, J=8.5 Hz, 2H), 7.91 (d, J=8.5 Hz, 2H), 7.35-7.25 (m, 15H), 7.01 (s, 1H), 4.59 (s, 2H), 3.57 (s, 1H), 3.49-3.40 (m, 1H), 1.29 (d, J=12.1 Hz, 2H) and 1.17 (d, J=6.8 Hz, 6H) ppm; MS (ES+) 559.17

Provenance & Evidence