tert-Butyl carbamate → HCID 86669027, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-chloro-2-(2-chloro-6-fluoro-4-iodo-phenyl)thiazolo[5,4-c]pyridine (715 mg, 1.682 mmol), tert-butyl carbamate (394 mg, 3.365 mmol), Pd2(dba)3 (77 mg, 0.084 mmol), and XantPhos (97 mg, 0.168 mmol) in toluene (17 mL) and K3PO4 (2.65 mL, 1.27 M) was heated at 90° C. under nitrogen for 20 hours. The reaction mixture was diluted with water, extracted with EtOAc (2×). The combined organics were dried (Na2SO4), filtered and concentrated. The crude product was purified by silica gel flash chromatography (0-25% EtOAc/hexane) to give the title compound (550 mg, 78.9% yield) as an off-white solid. 1H NMR (400 MHz, CDCl3) δ 8.48 (d, J=5.6 Hz, 1H), 7.95 (d, J=5.6 Hz, 1H), 7.46-7.33 (m, 2H), 6.70 (s, 1H), 1.55 (s, 9H). LCMS (ESI) m/z 414.1 [M+H+].

Provenance & Evidence