1-Tributylstannyl-imidazo[1,5-a]pyridine → 2-imidazo[1,5-a]pyridin-1-yl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamide

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-tributylstannyl-imidazo[1,5-a]pyridine (250 mg, 0.61 mmol) and 2-bromo-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamide (150 mg, 0.35 mmol) in DMF (2 mL) were added Pd(PPh3)4 (20 mg, 0.018 mmol) and copper(I) iodide (13 mg, 0.07 mmol). The reaction mixture was heated at 90° C. for 2 h then cooled to room temperature overnight. The reaction was quenched with water and extracted with EtOAc (3×). The combined organics were washed with water (3×) then dried over MgSO4 and concentrated. The residue was chromatographed once with 0% to 3% MeOH/CH2Cl2 (0.5% NH4OH) and then with 30% to 60% EtOAc/hexanes to afford 74 mg (45%) of 2-imidazo[1,5-a]pyridin-1-yl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamide as a bright yellow solid. 1H NMR (CDCl3, 300 MHz): δ (ppm) 9.35 (s, 1H), 8.53 (d, J=9.4 Hz, 1H), 8.38 (s, 1H), 8.32 (s, 1H), 8.12 (d, J=7.2 Hz, 1H), 8.05 (s, 1H), 6.99 (dd, J=9.4, 6.6 Hz, 1H), 6.77-6.87 (m, 1H), 5.74 (s, 2H), 3.54-3.68 (m, 2H), 1.67 (s, 9H), 0.90-1.06 (m, 2H), 0.00 (s, 9H).

Provenance & Evidence