4-Fluorophenylboronic acid → HCID 67497314, compound

Participants

Reaction Conditions

Reaction Steps

Bromide 44.A (200 mg, 0.44 mmol), 4-fluorophenylboronic acid (68 mg, 0.49 mmol), and Pd(dppf)Cl2 were mixed in THF and Na2CO3 (2 M). The resulting mixture was heated in a sealed tube in a microwave at 135° C. for 10 minutes. The organic layer was concentrated and the residue was partially purified on a silica gel column (12 g, 0-10% MeOH:DCM). The fractions containing desired product were combined, concentrated, and purified again on a prepHPLC (C18, ACN:H2O:0.1% TFA, gradient). The desired fractions were combined and concentrated on a rotavap to remove ACN and then partitioned with NaHCO3 (sat)/EtOAc. The organic layer was dried with sodium sulfate, filtered, and concentrated to yield 44 (18 mg). LC-MS (+esi, M+H+=432.1). 1H NMR (500 MHz, DICHLOROMETHANE-d2) δ ppm 9.63 (br. s., 1H) 8.71 (d, J=1.96 Hz, 1H) 7.86 (t, J=1.96 Hz, 1H) 7.54-7.64 (m, 3H) 7.40 (t, J=7.82 Hz, 1H) 7.28-7.33 (m, 3H) 7.24-7.28 (m, 1H) 7.22 (d, J=6.85 Hz, 2H) 7.12-7.18 (m, 2H) 7.04 (d, J=1.71 Hz, 1H) 3.84-3.94 (m, 2H) 3.54 (dd, J=9.41, 4.28 Hz, 1H) 3.27 (dd, J=13.94, 4.16 Hz, 1H) 2.85 (dd, J=14.06, 9.41 Hz, 1H).

Provenance & Evidence