Hydrochloric Acid → 3-bromo-1H-pyrrolo[3,2-b]pyridine-6-carboxylic acid hydrochloride

HRID 2403702Notes

Reaction equation

HRID 2403702 reaction equation
[Br:1][C:2]1[C:6]2=[N:7][CH:8]=[C:9]([C:11]([O:13]C)=[O:12])[CH:10]=[C:5]2[NH:4][CH:3]=1.[ClH:15]>O1CCOCC1>[ClH:15].[Br:1][C:2]1[C:6]2=[N:7][CH:8]=[C:9]([C:11]([OH:13])=[O:12])[CH:10]=[C:5]2[NH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 53412551methyl 3-bromo-1H-pyrrolo[3,2-b]pyridine-6-carboxylate

Product 1

HCID 708961403-bromo-1H-pyrrolo[3,2-b]pyridine-6-carboxylic acid hydrochlorideYield 87.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of methyl 3-bromo-1H-pyrrolo[3,2-b]pyridine-6-carboxylate (2.90 g, 11.4 mmol) in 1,4-dioxane (30 mL) was added 6 N aqueous hydrochloric acid (18.9 mL, 114 mmol). The reaction was heated to 90° C. and stirred overnight. The reaction was cooled to room temperature and concentrated to dryness to afford the title compound (2.76 g, quantitative). 1H NMR (400 MHz, DMSO-d6, δ): 12.31 (br. s., 1 H), 8.91 (d, J=1.8 Hz, 1 H), 8.37 (s, 1 H), 8.14 (d, J=1.6 Hz, 1 H).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-612c4a7c391f4840966e0138f58ab1fe
Source dataset
uspto-grants-2014_08
Patent number
US08802688B2

Reaction notes

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