Sodium Carbonate → 3-(6-methyl-1H-benzimidazol-2-yl)-5-[(E)-prop-1-enyl]pyrazin-2-amine

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-bromo-3-(6-methyl-1H-benzimidazol-2-yl)pyrazin-2-amine (50 mg, 0.1644 mmol), prop-1-enylboronic acid (15.53 mg, 0.1808 mmol), dichloropalladium; triethylphosphane (6.800 mg, 0.01644 mmol) and disodium carbonate (164.4 μL of 2 M, 0.3288 mmol) was dissolved in 1,2-dimethoxyethane (2 mL) and heated at 120° C. under microwave conditions 30 minutes. The residual solids were removed by filtration and the filtrate purified by reverse phase preparative HPLC [Waters Sunfire C18, 10 mM, 100 Å column, gradient 10%-95% B (solvent A: 0.05% TFA in water; solvent B: CH3CN) over 16 minutes at 25 mL/min]. The fractions were collected and freeze-dried to give the title compound as an orange solid (13.7 mg, 31% Yield). 1H NMR (400.0 MHz, DMSO) δ 1.95 (3H, d), 2.45 (3H, s), 6.45-6.55 (1H, m), 6.8-6.9 (1H, m), 6.95 (0.5H, m), 7.05-7.15 (2H, m), 7.22 (0.5H, s), 7.45 (1H, br s), 7.55-7.6 (1H, m), 8.1 (1H, s), 13.15 (1H, vbr s) ppm; MS (ES+) 266.0.

Provenance & Evidence