1,2-Dimethoxyethane → HCID 86662083, compound

Participants

Reaction Steps

A mixture of 3,5-dibromopyrazin-2-amine (200 mg, 0.7908 mmol), tert-butyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indole-1-carboxylate (271.4 mg, 0.7908 mmol), NaHCO3 (199.3 mg, 2.372 mmol) and palladium; triphenylphosphane (45.69 mg, 0.03954 mmol) in dimethoxyethane (2.000 mL) and water (1.000 mL) was heated at 120° C. in the microwave for 10 minutes. The reaction was diluted with EtOAc/water and the layers separated. The aqueous layer was extracted further with EtOAc (2×), dried (MgSO4) and concentrated in vacuo. The residue was taken up in DCM (5 mL), treated with BOC anhydride (517.7 mg, 544.9 μL, 2.372 mmol) and DMAP (9.661 mg, 0.07908 mmol) and allowed to stir overnight at ambient temperature. The reaction was concentrated in vacuo and the resultant residue was purified on silica gel by flash column chromatography (0-10% EtOAc/Petrol) to afford the product as a bright yellow solid (254 mg, 55% Yield). 1H NMR (DMSO) d 1.33 (18H, s), 1.53 (9H, s), 6.90 (1H, s), 7.26 (1H, m), 7.38 (1H, m), 7.58 (1H, m), 8.21 (1H, m) 8.56 (1H, s); MS (ES+) 590.89

Provenance & Evidence