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

HRID 930835

Reaction equation

HRID 930835 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 Example 1c (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 diethylether, filtered, and rinsed with additional diethylether and dried to provide the title compound (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 diethylether
  4. filtrationfiltered
  5. washrinsed with additional diethylether
  6. customdried

Sources & evidence

ORD record
ord-ede04b1e8a7f40ba94f817619411fce3
Source dataset
uspto-grants-2016_03
Patent number
US09296741B2

Linked notes

Loading…