Triethylamine → Methyl 2-(2-bromo-5-(3-nitro-4-(phenylethynyl)benzoyl)thiophen-3-yl)acetate

Participants

Reaction Steps

A solution of 2 (150 mg, 0.29 mmol), phenylacetylene (32 μL, 0.29 mmol), Pd(PPh3)2Cl2 (21 mg, 0.03 mmol), K2CO3 (42 mg, 0.29 mmol), and Et3N (40 μL, 0.29 mmol) in DMF (3 mL) was stirred for 24 hours at room temperature. Water (5 mL) was added to the mixture and then extracted with EtOAc (3×10 mL). The combined organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo. MPLC purification (Hex:EtOAc/5:1) of the residue gave 3 as a solid foam (101 mg, 71%). 1H NMR (400 MHz, CDCl3) δ 8.54 (d, J=1.6 Hz, 1H), 8.06 (dd, J=1.6, 8.0 Hz, 1H), 7.86 (d, J=8.4 Hz, 1H), 7.64 (m, 2H), 7.52 (s, 1H), 7.42 (m, 3H), 3.75 (s, 3H), and 3.70 (s, 2H); 13C NMR (100 MHz, CDCl3) δ 183.9, 170.1, 149.5, 142.2, 137.0, 136.3, 135.7, 135.3, 132.9, 132.5, 130.1, 128.8, 125.6, 124.3, 122.8, 122.1, 101.1, 84.7, 52.7, and 35.0.

Provenance & Evidence