Hydrochloric Acid → 4-Bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-B]pyridine

HRID 244639Notes

Reaction equation

HRID 244639 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][N:7]=[C:6]2[NH:10][CH:11]=[CH:12][C:5]=12.[C:13]1([S:19](Cl)(=[O:21])=[O:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.Cl>C1COCC1>[Br:3][C:4]1[CH:9]=[CH:8][N:7]=[C:6]2[N:10]([S:19]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)(=[O:21])=[O:20])[CH:11]=[CH:12][C:5]=12

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 222736434-Bromo-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 450745614-Bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-B]pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a stirred suspension of sodium hydride (1.12 g; 60% dispersion in mineral oil) in THF (3 ml) kept below 15° C., a suspension of 4-bromo-1H-pyrrolo[2,3-b]pyridine (5 g) (prepared for example, according to the method described in Organic Letters, 2003, 5, 5023) in THF (27 ml) was added over 20 minutes. The reaction was left to stir for 10 minutes. Then a solution of benzenesulfonyl chloride (3.6 ml) in THF (6 ml) was added over 5 minutes. The reaction was left to stir at RT for 1 hour, then 0.5M hydrochloric acid solution (10 ml) was added. The layers were separated and the organic layer washed with brine, dried over magnesium sulphate and the solvent removed in vacuo and left on the vacuum line for 3 days. The solid was triturated using methanol (30 ml) then dried in the oven for 5 hours to give the title compound as a pale pink solid (7.42 g).

Workup

  1. customkept below 15° C.
  2. additionwas added over 20 minutes
  3. waitThe reaction was left
  4. waitThe reaction was left
  5. stirringto stir at RT for 1 hour
  6. customThe layers were separated
  7. washthe organic layer washed with brine
  8. dry with materialdried over magnesium sulphate
  9. customthe solvent removed in vacuo
  10. waitleft on the vacuum line for 3 days
  11. customThe solid was triturated
  12. customthen dried in the oven for 5 hours

Sources & evidence

ORD record
ord-4ff58cd282fd41cab3d51df3a7659611
Source dataset
uspto-grants-2014_02
Patent number
US08658635B2

Reaction notes

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