Dimethylformamide → HCID 178518306, compound

Participants

Reaction Steps

A mixture of example 180 (151.11 mg, 0.344 mmol), 3-thiophene boronic acid (52.83 mg, 0.413 mmol), tetrakis(triphenylphosphine)palladium(0) (39.77 mg, 0.034 mmol) and Na2CO3 (72.93 mg, 0.688 mmol) in 3 mL 80% N,N-dimethylformamide (DMF)/H2O is reacted in microwave at 150° C. for 6 minutes. The reaction mixture is partition in ethyl acetate/water. The aqueous layer is separated and extracted 2 times with ethyl acetate. The combined organic extracts were evaporated in vacuo. The resulting residue is treated with 1 mL MeOH/CH2Cl2, and the fine solid precipitated out of solution. It is allowed to sit at room temperature overnight. The precipitate is filtered to get 86.4 mg (56.7%) product as a yellow solid. MS (ESI) m/z 441.1 (M−H)−1; HRMS: calcd for C22H16F2N2O4S+H+, 443.08716. found (ESI FT, [M+H]1+), 443.08671; 1H NMR (400 MHz, DMSO-D6) ppm 4.67 (d, J=6.29 Hz, 2 H) 6.78-6.86 (m, 1 H) 6.94-7.03 (m, 1 H) 7.08-7.20 (m, 1 H) 7.55 (dd, J=8.31, 1.51 Hz, 1 H) 7.68-7.73 (m, 1H) 7.77 (dd, J=5.04, 1.26 Hz, 1 H) 7.99 (d, J=8.31 Hz, 1 H) 8.08-8.16 (m, 2 H) 8.80 (d, J=13.09 Hz, 1 H) 10.01 (s, 1 H) 10.59-10.75 (m, 1 H) 10.99 (s, 1 H);

Provenance & Evidence