Hydrochloric Acid → 4-bromo-1-tosyl-1H-pyrrolo[2,3-c]pyridin-7(6H)-one

HRID 632740Notes

Reaction equation

HRID 632740 reaction equation
[Br:1][C:2]1[CH:7]=[N:6][C:5]([O:8]C)=[C:4]2[N:10]([S:13]([C:16]3[CH:22]=[CH:21][C:19]([CH3:20])=[CH:18][CH:17]=3)(=[O:15])=[O:14])[CH:11]=[CH:12][C:3]=12.Cl>O1CCOCC1>[Br:1][C:2]1[C:3]2[CH:12]=[CH:11][N:10]([S:13]([C:16]3[CH:22]=[CH:21][C:19]([CH3:20])=[CH:18][CH:17]=3)(=[O:15])=[O:14])[C:4]=2[C:5](=[O:8])[NH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 896575464-bromo-7-methoxy-1-tosyl-1H-pyrrolo[2,3-c]pyridine

Product 1

HCID 896575804-bromo-1-tosyl-1H-pyrrolo[2,3-c]pyridin-7(6H)-oneYield 94%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
40 °C

Procedure

A solution of 4-bromo-7-methoxy-1-tosyl-1H-pyrrolo[2,3-c]pyridine (12.4 g, 32.6 mmol) in dioxane (140 mL) was stirred at room temperature. To this solution was added 4M HCl in dioxane (140 mL). The reaction mixture was stirred at 40° C. for 16 hours. The reaction mixture was cooled to room temperature and concentrated. The residue was triturated with diethyl ether, filtered, and rinsed with additional diethyl ether and dried to provide 4-bromo-1-tosyl-1H-pyrrolo[2,3-c]pyridin-7(6H)-one (11.23 g, 30.6 mmol, 94% yield) as a beige solid.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated
  3. customThe residue was triturated with diethyl ether
  4. filtrationfiltered
  5. washrinsed with additional diethyl ether
  6. customdried

Sources & evidence

ORD record
ord-57595f7256514b2382a70bcb8fcd7655
Source dataset
uspto-grants-2016_04
Patent number
US09321765B2

Reaction notes

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