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

HRID 1780588Notes

Reaction equation

HRID 1780588 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

4

Reactant 3

HCID 10340Sodium CarbonateHCID 19047050N-[2-(6-Chloro-2-pyrazinyl)-4-methylphenyl]-2,2-dimethylpropanamideHCID 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).

Workup

  1. extractionextracted with ethyl acetate (5×50 mL)
  2. dry with materialThe combined extracts were dried (MgSO4)
  3. customevaporated
  4. customThe solid residue was recrystallized from hexane

Sources & evidence

ORD record
ord-c9569bcb07884fe4826d5e30f0fcc607
Source dataset
uspto-grants-1997_05
Patent number
US05631206

Reaction notes

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