Water → HCID 46869361, compound

Participants

Reaction Conditions

Reaction Steps

To a 25 ml of flask was added ethyl 2-((S)-1-(3-bromophenylamino)-1-oxo-3-phenylpropan-2-ylamino)acetate 107.1.B (165 mg, 0.41 mmole), pyridine-4-yl boronic acid (53 mg, 0.43 mmole), tetrakis(triphenylphosphine)palladium (94 mg, 0.081 mmole), potassium carbonate (112 mg, 0.81 mmole), 0.2 ml of water and 2 ml of N,N-dimethylacetamide. The reaction mixture was stirred at 80° C. for 5 hours. Then, the reaction mixture was diluted with ethyl acetate. The organic layer was washed with water and brine, and dried over anhydrous sodium sulfate. After concentration in vacuo, the residue was chromatographed on silica gel to give 107.1.C (26 mg, 16% yield). 1H NMR (400 MHz, CDCl3) δ ppm 9.53 (s, 1H), 8.67 (d, J=5.8 Hz, 2H), 8.01 (s, 1H), 7.70-7.27 (m, 10H), 4.17-4.10 (m, 2H), 3.50 (dd, J=9.0, 4.3 Hz, 1H), 3.36 (s, 2H,), 3.35 (dd, J=14.1, 4.3 Hz, 1H), 2.92 (dd, J=14.1, 9.0 Hz, 1H), 1.99 (brs, 1H), 1.22 (t, J=7.2 Hz, 3H).

Provenance & Evidence