Cyclopentanol → HCID 89783914, compound

Participants

Reaction Steps

Similar to the method described in Example 103, cyclopentanol (0.18 mL, 2.02 mmol) was added to a suspension of NaH (60% w/w in mineral oil) (81 mg, 2.02 mmol) in DMF (2.0 mL) and the resulting light-yellow solution was stirred at RT for 10 min. 2-(2-Chloroquinolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (Example 1; 75 mg, 0.25 mmol) was then added and the resulting dark red solution was stirred at RT for 5 min, then heated at 70° C. for 3 h. The mixture was cooled to RT and partitioned between EtOAc (70 mL) and saturated aq. NH4Cl (50 mL). The organic layer was separated, sequentially washed with water (20 mL) and brine (20 mL), and then dried over MgSO4, filtered, and concentrated in vacuo. The crude residue was purified by column chromatography silica gel column, 10-100% EtOAc in hexanes over 25 min. then 100% EtOAc for 10 min.) to give 2-(2-(cyclopentyloxy)quinolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (30 mg, 0.09 mmol, 33.8% yield) as an amorphous yellow solid: 1H NMR (400 MHz, CDCl3) δ ppm 12.70 (br. s., 1H), 7.95-8.10 (m, 2H), 7.51-7.59 (m, 1H), 7.36-7.45 (m, 1H), 7.17 (d, J=2.0 Hz, 1H), 6.90 (d, J=8.8 Hz, 1H), 5.57 (br. s., 1H), 5.44 (quin, J=4.4 Hz, 1H), 3.68 (t, J=6.7 Hz, 2H), 2.98 (t, J=6.8 Hz, 2H), 2.02-2.16 (m, 4H), 1.84-1.98 (m, 2H), 1.67-1.80 (m, 2H). m/z (ESI, +ve ion) 348.0 (M+H)+.

Provenance & Evidence