Sodium hydride → US9907800, Example A12

Participants

Reaction Steps

To a mixture of trimethylsulfoxonium iodide (220 mg, 1 mmol) and 60% NaH (120 mg, 3 mmol) in a RBF was added DMF (5 mL). The resulting mixture was stirred for 5 min at rt. A solution of (E & Z)-3-((1H-indazol-6-yl)methylene)-5-bromo-1H-pyrrolo[2,3-b]pyridin-2(3H)-one (170 mg, 0.5 mmol) in DMF (5 mL) was added. After addition, the resulting mixture was heated at 55° C. (oil temp.) for 2.5 h. Upon cooling to 0° C., it was quenched with ice, sat. NH4Cl, extracted with EtOAc (50 mL×2). Combined extracts were dried (Na2SO4) and concentrated to give light brown liquid. The residue was purified by flash chromatography (eluent: CH2Cl2/MeOH/Et3N 100:5:1 to 100:10:1) to give the title compound as a pale yellow oil which was triturated with CH2Cl2. The resulting precipitates were collected by suction filtration and dried to give the title compound (66 mg, 37%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 13.07 (s, 1H), 11.42 (s, 1H), 8.04 (s, 1H), 8.02 (d, J=2.0 Hz, 1H), 7.68 (d, J=8.4 Hz, 1H), 7.51 (s, 1H), 6.98 (d, J=8.0 Hz, 1H), 6.44 (d, J=2.0 Hz, 1H), 2.60 (dd, J=8.0 Hz, J=4.4 Hz, 1H), 2.10 (dd, J=8.8 Hz, J=4.8 Hz, 1H); MS ESI 355.1 [M+H]+, calcd for [C16H11BrN4O+H]+ 355.0.

Provenance & Evidence