2,3-Dihydrofuran → HCID 68162420, compound

Participants

Reaction Conditions

Reaction Steps

A solution of PU-H71 (30 mg, 0.0585 mmol) in NMP (1.5 mL) was evacuated and back filled with nitrogen. This was repeated four times, then DIEA (15.1 mg, 21 μL, 0.117 mmol), 2,3-dihydrofuran (82 mg, 88 μL, 1.17 mmol) and Pd(PPh3)4 (13.5 mg, 0.0117 mmol) were added and the reaction mixture was heated under nitrogen at 55° C. for 20 h. Solvent was removed under reduced pressure and the resulting residue was purified by preparatory TLC two times (hexane:EtOAc:CH2Cl2:MeOH—NH3 (7N), 2:1:2:0.5, then CH2Cl2:MeOH—NH3 (7N), 15:1) to give 7.0 mg (26%) of DZ3-142. 1H NMR (500 MHz, CDCl3) δ 8.23 (s, 1H), 7.06 (s, 1H), 6.96 (s, 1H), 6.43 (m, 1H), 6.01 (s, 2H), 5.94 (dd, J=8.1, 10.8 Hz, 1H), 5.72 (br s, 2H), 4.93 (m, 1H), 4.35 (t, J=6.8 Hz, 2H), 2.95-3.55 (m, 2H), 2.70 (t, J=6.5 Hz, 2H), 2.39-2.47 (m, 1H), 2.22 (m, 2H), 1.25 (d, J=6.2 Hz, 6H); HRMS (ESI) m/z [M+H]+ calcd. for C22H27H6O3S, 455.1865; found. 455.1865; HPLC: method A Rt=6.07, method B Rt=6.49.

Provenance & Evidence