o-Toluenesulfonyl chloride → HCID 49758932, compound

HRID 1409108Notes

Reaction equation

HRID 1409108 reaction equation
[Br:1][C:2]1[C:7]([Cl:8])=[CH:6][N:5]=[C:4]2[NH:9][CH:10]=[CH:11][C:3]=12.[H-].[Na+].[C:14]1(C)[C:15]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:17]=[CH:18][CH:19]=1.[CH3:25]COC(C)=O>CN(C=O)C>[Br:1][C:2]1[C:7]([Cl:8])=[CH:6][N:5]=[C:4]2[N:9]([S:20]([C:15]3[CH:14]=[CH:19][C:18]([CH3:25])=[CH:17][CH:16]=3)(=[O:21])=[O:22])[CH:10]=[CH:11][C:3]=12

Participants

6

Reactant 4

HCID 8623o-Toluenesulfonyl chlorideHCID 8857Ethyl AcetateHCID 24758Sodium hydride2×HCID 468355224-Bromo-5-chloro-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 49758932HCID 49758932, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-bromo-5-chloro-1H-pyrrolo[2,3-b]pyridine (D) (1.89 g, 8.16 mmol) in DMF (15 mL) at 0° C. was added NaH (60% in oil, 328 mg) followed by toluenesulfonylchloride (1.72 g, 8.98 mmol). The reaction mixture was warmed to RT and additional NaH (60% in oil, 2×200 mg) was added at 1 h intervals. After a further 1 h, EtOAc was added and the reaction was quenched with sat'd NaHCO3. The aqueous layer was extracted with EtOAc and the combined organic layer was washed with water, brine, dried over Na2SO4, filtered and concentrated. Flash chromatography (SiO2, 7% EtOAc in hexanes) provided 4-bromo-5-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridine (E) (1.81 g, 58%) as an off white solid. LC/MS Tret=4.8 min, (M+H+) 386.6.

Workup

  1. customthe reaction was quenched with sat'd NaHCO3
  2. extractionThe aqueous layer was extracted with EtOAc
  3. washthe combined organic layer was washed with water, brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-efdc30931e6f4d3bb80dbc35aa63f81c
Source dataset
uspto-grants-2014_12
Patent number
US08921376B2

Reaction notes

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