Potassium Phosphate, Tribasic → HCID 59618747, compound

Participants

Reaction Steps

A mixture of intermediate 25 (30 mg, 0.06 mmol), 3-pyridine boronic acid (74 mg, 0.60 mmol), Pd(OAc)2 (13 mg, 0.06 mmol), S-Phos (49 mg, 0.12 mmol) and K3PO4 (100 mg) in 4 mL 99:1 v:v toluene/H2O was heated at 150° C. for 40 min in a microwave reactor. After cooling to rt, the reaction mixture was concentrated and the residue was purified by silica gel chromatography (10-100% EtOAC/hexanes) to afford the title compound as a racemic mixture. 1H NMR (500 MHz, (CD3)2CO): δ 8.62 (s, 1H), 8.58 (d, 1H), 8.42 (s, 1H), 7.82 (d, 1H), 7.75 (d, 1H), 7.40 (m, 2H), 7.20 (d, 2H), 7.16 (d, 1H), 7.14 (m, 1H), 7.02 (d, 2H), 5.20 (d, 1H), 4.85 (d, 1H), 1.23 (s, 9H). LC-MS: m/z 539.2 (M+H)+. The racemic mixture was separated by HPLC using a chiralcel OD-H column and 20% EtOH/hexanes as the mobile phase. The fastest eluting isomer (E1) has a retention time of 12.0 min, the slower eluting isomer (E2) has a retention time of 20 min.

Provenance & Evidence