Acetonitrile → HCID 71661721, compound

Participants

Reaction Steps

A mixture of 5-azido-2-(thiazol-5-yl) benzo[d]oxazole 29 (37 mg, 0.15 mmol) and (But-3-yn-2-yloxy) Benzene 28 (20 mg, 0.13 mmol) were dissolved in anhydrous acetonitrile (3 mL) under nitrogen atmosphere. Then added DIPEA (53 mg, 0.40 mmol) stirred at rt for 10 min. After that added CuI (51.7 mg, 0.27 mmol) portion wise, stirred for 30 mins. The mixture was quenched with NH4Cl, diluted with water and extracted with DCM. Organic layer dried on MgSO4, filtered and concentrated under vacuo. Corresponding crude product was isolated by using silica column (ethyl acetate/n-hexane 50:50) to furnish 5-(4-(1-phenoxyethyl)-1H-1, 2,3-triazol-1-yl)-2-(thiazol-5-yl) benzo [d]oxazole 30 (43 mg, 84%) as a solid. 1H NMR (CDCl3, 400 MHz) δ 1.77 (d, J=6.4 Hz, 3H), 5.69 (q, J=6.4 Hz, 1H), 6.90-6.97 (m, 3H), 7.22-7.24 (m, 2H), 7.66 (d, J=8.8 Hz, 1H), 7.74 (dd, J1=8 Hz, J2=2 Hz, 1H), 7.90 (s, 1H), 7.99 (d, J=2 Hz, 1H), 8.66 (s, 1H), 8.98 (s, 1H); 13C NMR (Pyridine-d5, 100 MHz) δ 22.1, 69.5, 112.3, 112.5, 116.6, 119.1, 121.7, 121.8, 125.8, 130.3, 135.3, 143.2, 146.9, 150.5, 151.1, 158.5, 159.0, 159.3; ESI-HRMS for C20H16N5O2S (M+H)+ calcd. 390.1025. found 390.1031.

Provenance & Evidence