Sodium Carbonate → 2-Ethynyl-6-(4-(isopropylsulfonyl)phenyl)pyrazine

HRID 522531Notes

Reaction equation

HRID 522531 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[CH:7]([S:10]([C:13]1[CH:18]=[CH:17][C:16]([C:19]2[N:24]=[C:23]([C:25]#[C:26][Si](C)(C)C)[CH:22]=[N:21][CH:20]=2)=[CH:15][CH:14]=1)(=[O:12])=[O:11])([CH3:9])[CH3:8]>CO.CCOC(C)=O.O>[C:25]([C:23]1[CH:22]=[N:21][CH:20]=[C:19]([C:16]2[CH:17]=[CH:18][C:13]([S:10]([CH:7]([CH3:9])[CH3:8])(=[O:12])=[O:11])=[CH:14][CH:15]=2)[N:24]=1)#[CH:26]

Participants

6

Reactant 2

HCID 10340Sodium CarbonateHCID 674806192-(4-(Isopropylsulfonyl)phenyl)-6-((trimethylsilyl)ethynyl)pyrazine

Product 1

HCID 866651492-Ethynyl-6-(4-(isopropylsulfonyl)phenyl)pyrazineYield 98%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium carbonate (3 mL of 2 M, 6.000 mmol) was added to a stirred suspension of 2-[6-(4-isopropylsulfonylphenyl)pyrazin-2-yl]ethynyl-trimethyl-silane (191 mg, 0.5327 mmol) in methanol (6 mL) and the reaction was stirred at ambient temperature for 45 minutes. The reaction mixture was diluted with EtOAc and water and the layers separated. The aqueous layer was extracted with EtOAc and the combined organic extracts were washed with brine, dried (MgSO4), filtered and concentrated in vacuo to give the sub-title compound as a beige solid (149 mg, 98% Yield). 1H NMR (400.0 MHz, DMSO) d H NMR (400.0 MHz, DMSO) d 9.38 (s, 1H); 8.86 (s, 1H), 8.40 (d, 2H), 8.01 (d, 2H), 4.78 (s, 1H), 3.50 (sept, 1H) and 1.18 (d, 6H) ppm; MS (ES+) 297.1

Workup

  1. customthe layers separated
  2. extractionThe aqueous layer was extracted with EtOAc
  3. washthe combined organic extracts were washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5680e0cdace64da98a2ea03d3637ed61
Source dataset
uspto-grants-2016_05
Patent number
US09334244B2

Reaction notes

Loading…