Tetrahydrofuran → HCID 178517433, compound

Participants

Reaction Steps

A mixture of 3-hydroxyisoquinoline (84.3 mg, 0.581 mmol) and 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (236 mg, 0.666 mmol) in THF (6.0 mL, 74 mmol) was stirred at ambient temperature for 17 d. More 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (25 mg, 0.070 mmol) was added, and the reaction mixture was heated to 50° C. for 1d. Solid material was filtered off and rinsed with THF. The filtrate was diluted with DCM (≈75 mL), washed with water (2×) and brine, dried over MgSO4, filtered, and dried in vacuo overnight. One obtained the title compound as yellow solid. It was used in the next step without further purification. 1H NMR (400 MHz, DMSO-d6): δ=11.54 (brs, 1H), 8.75 (s, 1H), 8.01 (d, J=8.4 Hz, 1H), 7.84 (d, J=8.0 Hz, 1H), 7.69 (t, J=8.0 Hz, 1H), 7.40 (t, J=7.6 Hz, 1H). MS(ES+): m/z=164.03 (100) [MH+]. HPLC: tR=2.2 min (polar—5 min, ZQ3).

Provenance & Evidence