Sodium Carbonate → 3-(6-methyl-1H-benzo[d]imidazol-2-yl)-5-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)pyrazin-2-amine

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Reaction Steps

A mixture of 5-bromo-3-(6-methyl-1H-benzimidazol-2-yl)pyrazin-2-amine (150 mg, 0.4932 mmol), 1,4-dioxaspiro[4.5]dec-7-en-8-ylboronic acid (181.5 mg, 0.9864 mmol), dichloropalladium; triethylphosphane (10.20 mg, 0.02466 mmol) and Na2CO3 (740.0 μL of 2 M, 1.480 mmol) were heated in DMF (1.500 mL) at 130° C. in a microwave for 30 min. EtOAc was added and the organic phase washed with saturated aqueous Na2CO3, dried (MgSO4) and concentrated in vacuo. The resulting oil was purified by reverse phase preparative HPLC [Waters Sunfire C18, 10 uM, 100A 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 a yellow solid (113 mg, 63% Yield). 1H NMR (400.0 MHz, DMSO) d 1.86 (t, J=6.4 Hz, 2H), 2.45 (m, 5H), 2.76 (s, 2H), 3.95 (s, 4H), 6.61 (t, J=3.9 Hz, 1H), 7.07 (dd, J=1.3, 8.3 Hz, 1H), 7.38 (s, 1H), 7.48 (d, J=8.2 Hz, 1H), 7.54 (s, 1H), 7.62 (d, J=8.3 Hz, 1H), 8.31 (d, J=4.0 Hz, 1H) and 8.37 (s, 1H) ppm; MS (ES+) 364

Provenance & Evidence