Dichloromethane → HCID 58710067, compound

Participants

Reaction Steps

To a stirred solution of tert-butyl 4-[4-(3-iodo-4-methoxyphenylamino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-3,6-dihydro-2H-pyridine-1-carboxylate (82.1 mg, 0.15 mmol), N-Boc-2-pyrrolylboronic acid (47.5 mg, 0.225 mmol) and potassium carbonate (41.5 mg, 0.3 mmol) in dioxane/water (4:1) (11.0 mL) was added PdCl2(dppf).CH2Cl2 (12.2 mg, 0.015 mmol). The mixture was heated at reflux for 18 h. Solvents were removed and the residue was dissolved in DMF (≈2 mL). The DMF solution was filtered and sent to mass-directed HPLC purification. The pyrrole-Boc-protected product obtained was stirred with NaOH (s, 369 mg) in 9 mL of methanol at rt for 17 h. The solvent was removed and the residue was dissolved in DMF (1.5 mL) and purified by HPLC purification to give the title compound. 1H-NMR (DMSO-d6, 400 MHz): δ=1.43 (s, 9H), 2.46 (m, 2H), 3.56 (m, 2H), 3.87 (s, 3H), 4.03 (m, 2H), 6.11 (q, J=2.4 Hz, 1H), 6.37 (s, br, 1H), 6.49 (s, 1H), 6.71 (s, 1H), 6.81 (q, J=2.4 Hz, 1H), 7.04 (d, J=9.2 Hz, 1H), 7.63 (d, J=6.0 Hz, 1H), 7.92 (d, J=2.4 Hz, 1H), 8.20 (d, J=4.4 Hz, 1H), 9.22 (s, 1H), 10.91 (s, 1H), 11.89 (s, 1H). MS (ES+): m/z 487.04 [MH+]. HPLC: tR=2.96 min (ZQ2000, polar—5 min).

Provenance & Evidence