Trimethylsilylacetylene → HCID 67981331, compound

Participants

Reaction Steps

A mixture of trimethylsilylacetylene (1.60 mL; 11.3 mmol; 2.1 eq.), tert-butyl 3-bromo-5-(hydroxymethyl)-1H-indazole-1-carboxylate (1.80 g; 5.50 mmol; 1.0 eq.), Pd(OAc)2 (54 mg; 0.24 mmol; 0.04 eq.), triphenylphosphine (115 mg; 0.44 mmol; 0.08 eq.) and Copper iodide (62 mg; 0.33 mmol; 0.06 eq.) in TEA (50 mL) was degassed then heated at reflux for 3 h. After cooling, it was poured into HCl (0.1 N solution) and extracted with EtOAc. Combined organic phases were washed with brine, dried over magnesium sulfate, filtered and concentrated to give the title compound as a brown oil (2.6 g). 1H NMR (300 MHz, DMSO-d6) δ 8.06 (d, J=8.7 Hz, 1H), 7.71 (s, 1H), 7.60 (dd, J=1.6, 8.7 Hz, 1H), 5.41 (t, J=5.7 Hz, 1H), 4.66 (d, J=5.7 Hz, 2H), 1.65 (s, 9H), 0.32 (s, 9H). MS (ESI+): 345.2.

Provenance & Evidence