Sodium Carbonate → N-[2-(6-Bromo-2-pyrazinyl)-4-methylphenyl]-2,2-dimethyl-propanamide

Reaction equation

Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[C:12]([CH3:14])[CH:11]=[CH:10][C:9]=2[NH:15][C:16](=[O:21])[C:17]([CH3:20])([CH3:19])[CH3:18])[CH:5]=[N:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[BrH:28].C(O)(=O)C>>[Br:28][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[C:12]([CH3:14])[CH:11]=[CH:10][C:9]=2[NH:15][C:16](=[O:21])[C:17]([CH3:20])([CH3:19])[CH3:18])[CH:5]=[N:4][CH:3]=1

Participants

Reactant 3

HCID 10340Sodium Carbonate

HCID 19047050N-[2-(6-Chloro-2-pyrazinyl)-4-methylphenyl]-2,2-dimethylpropanamide

HCID 21893785Acetic Acid Mixture with Hydrobromic Acid

Product 1

HCID 19047047N-[2-(6-Bromo-2-pyrazinyl)-4-methylphenyl]-2,2-dimethyl-propanamideYield 45%

Procedure

The product from Step A (2.0 g, 6.6 mmol) was dissolved in a 30% solution of hydrobromic acid/acetic acid (18.0 mL). This mixture was stirred at room temperature for four days. The mixture was poured into aqueous 1M sodium carbonate (150 mL) and then extracted with ethyl acetate (5×50 mL). The combined extracts were dried (MgSO4) and then evaporated. The solid residue was recrystallized from hexane to afford 1.0 g (45%) of the title compound melting at 74°-76° C. 1H NMR (400 MHz, CDCl3) δ 10.64 (br s, 1H), 8.92 (s, 1H), 8.66 (s, 1H), 8.38 (m, 1H), 729-7.43 (s, 1H), 7.29-7.32 (m, 1H), 2.39 (s, 3H), 1.33 (s, 9H). Mass spec (EI) m/e 349 (1XBr).