Sodium Carbonate → Benzamide, N,N-bis(1-methylethyl)-

Participants

Reaction Conditions

Reaction Steps

Bis amide 17. The 2,2-dimethyl-N-(4-iodo-3-pyridinyl)propanamide (700 mg, 2.3 mmol) and 2-diisopropylbenzamide boronic acid (1.3 g, 5.2 mmol) were dissolved in DMF. Tetrakis(triphenylphosphine)palladium (133 mg, 0.11 mmol) and 2 M sodium carbonate solution (2.2 mL) were added. The reaction was refluxed at 83° C. for 18 h The mixture was concentrated in vacuo, extracted with EtOAc, washed with brine and dried with sodium sulfate. The crude oil was chromatographed (CH2Cl2, 1%-5% MeOH/CH2Cl2) to obtain 2-[3-2,2-dimethyl-propionylamino)-pyridin-4-yl]-N,N-diisopropylbenzamide as a white solid. 1H NMR (DMSO-d6, 300 MHz) δ 9.08 (s, 1 H), 8.64 (s, 1 H), 8.43 (d, 1H), 7.58–7.48 (m, 2 H), 7.40 (dd, 1 H), 7.33 (d, 1 H), 7.24 (dd, 1 H), 3.53–3.36 (m, 2 H), 1.38 (d, 3 H), 1.01 (d, 3 H), 0.97 (s, 9 H), 0.91 (d, 3 H), 0.77 (d, 3 H); MS (ES+)=382.

Provenance & Evidence