4-Toluenesulfonyl chloride → 5-bromo-3-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridine

HRID 531431Notes

Reaction equation

HRID 531431 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([I:11])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[H-].[Na+].[S:14](Cl)([C:17]1[CH:23]=[CH:22][C:20]([CH3:21])=[CH:19][CH:18]=1)(=[O:16])=[O:15].C(OCC)(=O)C>CN(C=O)C.CCCCCC>[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([I:11])=[CH:9][N:8]([S:14]([C:17]3[CH:23]=[CH:22][C:20]([CH3:21])=[CH:19][CH:18]=3)(=[O:16])=[O:15])[C:5]2=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 242292125-Bromo-3-iodo-1H-pyrrolo(2,3-b)pyridine

Product 1

HCID 497590665-bromo-3-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridineYield 96.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent3×HCID 8058HexaneSolvent

Procedure

5-Bromo-3-iodo-1H-pyrrolo[2,3-b]pyridine (7 g, 21.6 mmol) dissolved in dry DMF (50 ml) was added drop wise to a stirred slurry of sodium hydride (1.73 g, 43.2 mmol) in dry DMF (20 ml) at 0° C. and stirred for 30 min. Tosyl chloride (6.15 g, 32.4 mmol) dissolved in dry DMF (14 ml) and added slowly to the above reaction mixture and the reaction temperature was brought to RT and stirred for 30 min. The reaction was monitored by TLC (15% Ethyl acetate in hexane). The reaction mixture was quenched with ice water (500 ml) at 0° C. and filtered the solid precipitated and dried under vacuum to afford 9.92 g (96.3% yield) of 5-bromo-3-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridine MS: m/z=476.8 (M+1).

Workup

  1. additionadded slowly to the above reaction mixture
  2. customwas brought to RT
  3. stirringstirred for 30 min
  4. customThe reaction mixture was quenched with ice water (500 ml) at 0° C.
  5. filtrationfiltered the solid
  6. customprecipitated
  7. customdried under vacuum

Sources & evidence

ORD record
ord-27a01fb27ce247cd953422da19621bc7
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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