4-Toluenesulfonyl chloride → 2-Bromo-7-iodo-5-tosyl-5H-pyrrolo[2,3-B]pyrazine

HRID 2389020Notes

Reaction equation

HRID 2389020 reaction equation
[Br:1][C:2]1[N:3]=[C:4]2[C:10]([I:11])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[H-].[Na+].[C:14]1([CH3:24])[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1>C1COCC1>[Br:1][C:2]1[N:3]=[C:4]2[C:10]([I:11])=[CH:9][N:8]([S:20]([C:17]3[CH:18]=[CH:19][C:14]([CH3:24])=[CH:15][CH:16]=3)(=[O:22])=[O:21])[C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 441182772-bromo-7-iodo-5H-pyrrolo(2,3-b)pyrazine

Product 1

HCID 457896312-Bromo-7-iodo-5-tosyl-5H-pyrrolo[2,3-B]pyrazineYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 2-Bromo-7-iodo-5H-pyrrolo[2,3-b]pyrazine (290 mg, 0.895 mmol) in THF (5 ml) was added NaH (60%, 43 mg, 1.08 mmol) in one portion at 0° C. The resulting mixture was stirred for 20 minutes before a solution of para-toluenesulfonyl chloride (188 mg, 0.98 mmol) in THF (2 mL) was added. The reaction mixture was then stirred at room temperature for 3 hours. Solvents were removed and the resulting dark brown residue washed with aqueous KOH, water and dried to afford the title compound (423 mg, 99% yield) as a light brown solid. 1H-NMR (500 MHz, d6-DMSO) δ 8.60 (d, 11.5 Hz, 1H), 7.99 (d, 11.5 Hz, 2H), 7.44 (d, 7.5 Hz, 2H), 2.34 (s, 3H). MS: m/z 477.8/479.8 [MH+].

Workup

  1. additionwas added
  2. customSolvents were removed
  3. washthe resulting dark brown residue washed with aqueous KOH, water
  4. customdried

Sources & evidence

ORD record
ord-4bf8ec7e4d184a1eaf7cbb44e375ad93
Source dataset
uspto-grants-2012_09
Patent number
US08268994B2

Reaction notes

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