Tetrahydrofuran → HCID 89682607, compound

Participants

Reaction Conditions

Reaction Steps

A round bottom flask was charged with 1,1,1,3,3,3-hexafluoropropan-2-yl 4-(4-bromo-2-morpholinobenzyl)piperazine-1-carboxylate (Example 57, 30 mg, 0.0562 mmol), Bis(diphenylphosphino)ferrocene-palladium(II)dichloride (5 mg, 6.13 μmol), phenylboronic acid (10 mg, 82.0 μmol), and K2CO3 (21 mg, 152 μmol). THF (4 mL) and H2O (0.4 mL) were added and the reaction was heated to 70° C. for 2 h. The reaction was diluted in CH2Cl2 and washed with sat Na2CO3 (2×) and brine (1×). The organics were dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was chromatographed on a silica gel column (100% to 80% hexanes in EtOAc) and yielded 1,1,1,3,3,3-hexafluoropropan-2-yl 4-((3-morpholino-[1,1′-biphenyl]-4-yl)methyl)piperazine-1-carboxylate (18 mg, 60%). 1H NMR 400 MHz (CDCl3) δ 7.54-7.48 (m, 2H), 7.45-7.34 (m, 3H), 7.31-7.20 (m, 3H), 5.68 (h, J=6.3 Hz, 1H), 3.84-3.71 (m, 4H), 3.57 (s, 2H), 3.53-3.39 (m, 4H), 3.00-2.93 (m, 4H), 2.47 (dt, J=9.9, 5.0 Hz, 4H). LCMS (ESI, m/z): 532 [M+H]+.

Provenance & Evidence