Dimethylformamide → HCID 178518303, compound

Participants

Reaction Steps

A mixture of example 180 (155.4 mg, 0.354 mmol), 3-furanboronic acid (47.51 mg, 0.425 mmol), tetrakis(triphenylphosphine)palladium(0) (40.46 mg, 0.035 mmol) and Na2CO3 (75.05 mg, 0.708 mmol) in 3 mL 80% N,N-dimethylformamide (DMF)/H2O is reacted in microwave at 150° C. for 6 minutes. The reaction mixture is partitioned 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 73.4 mg (48.6%) product as a yellow solid: MS (ESI) m/z 425.2 (M−H)−1; HRMS: calcd for C22H16F2N2O5+H+, 427.11001. found (EFI FT, [M+H]1+), 427.11023; 1H NMR (400 MHz, DMSO-D6) ppm 4.66 (d, J=6.30 Hz, 2 H) 6.70-6.90 (m, 1 H) 6.91-7.03 (m, 1 H) 7.06-7.23 (m, 2 H) 7.45 (dd, J=8.18, 1.38 Hz, 1 H) 7.82 (t, J=1.76 Hz, 1 H) 7.88-8.09 (m, 2 H) 8.36 (s, 1 H) 8.75 (d, J=13.09 Hz, 1 H) 10.02 (s, 1 H) 10.47-10.75 (m, 1H) 10.98 (s, 1 H); Analysis for C22H16F2N2O5: Calcd: C, 61.97; H, 3.78; N, 6.57. Found: C, 62.22; H, 3.74; N, 6.94.

Provenance & Evidence