4-Fluorophenyl isocyanate → HCID 59536314, compound

Participants

Reaction Steps

To a round-bottomed flask containing crude 1-(4-methoxyphenyl)-1,2,3,4-tetrahydroisoquinoline (25 mg, 104 μmol) and CH2Cl2 (10 mL) was added 1-fluoro-4-isocyanatobenzene (0.03 mL, 264 μmol). The solution was stirred at RT. After 1 h, the reaction was concentrated in vacuo and taken up in DMF and purified by reverse-phase preparative HPLC (Shimadzu) on a Phenomenex Gemini™ column (5 micron, C18, 110 Å, Axia, 100×50 mm) eluting at 90 mL/min with an linear gradient of 10% to 100% MeCN (0.1% TFA) in water (0.1% TFA) over 10 min to give crude product, that was lypholized and resubjected to the same purification conditions to give N-(4-fluorophenyl)-1-(4-methoxyphenyl)-3,4-dihydroisoquinoline-2(1H)-carboxamide, as a white solid that contained 0.66 eq of TFA. MS (ESI pos. ion) m/z: 377 (M+1).

Provenance & Evidence