Hydrochloric Acid → HCID 53412688, compound

HRID 634114Notes

Reaction equation

HRID 634114 reaction equation
[NH:1]1[C:9]2[C:4](=[N:5][C:6]([C:10]([OH:12])=[O:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[I:13]I.[OH-].[K+].S(=O)(O)[O-].[Na+].Cl>CN(C=O)C.O>[I:13][C:3]1[C:4]2=[N:5][C:6]([C:10]([OH:12])=[O:11])=[CH:7][CH:8]=[C:9]2[NH:1][CH:2]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 807IodineHCID 14797Potassium HydroxideHCID 23665763Sodium BisulfiteHCID 260764431H-Pyrrolo[3,2-b]pyridine-5-carboxylic acid

Product 1

HCID 53412688HCID 53412688, compoundYield 72.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1H-pyrrolo[3,2-b]pyridine-5-carboxylic acid (0.400 g, 2.467 mmol, Adesis, New Castle, Del.) in DMF (4.9 mL) was added I2 (0.626 g, 2.467 mmol) and KOH (0.346 g, 6.17 mmol). The mixture was stirred at RT for 1 h. The mixture was poured into ice and H2O (30 mL) containing sodium bisulfite (0.257 g, 2.467 mmol). The reaction was acidified with 5 M HCl. A yellow solid precipitated out and was collected by filtration, washed with H2O and dried overnight in a vacuum oven to give 3-iodo-1H-pyrrolo[3,2-b]pyridine-5-carboxylic acid (0.516 g, 1.791 mmol, 72.6%). MS (ESI, pos. ion) m/z: 289.0 (M+1). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.91 (2H, s), 8.01 (1H, d, J=2.74 Hz), 12.03-12.11 (1H, m).

Workup

  1. customA yellow solid precipitated out and
  2. filtrationwas collected by filtration
  3. washwashed with H2O
  4. customdried overnight in a vacuum oven

Sources & evidence

ORD record
ord-bbd52ebff2a04891bb046dbd8bbdc51e
Source dataset
uspto-grants-2016_04
Patent number
US09321756B2

Reaction notes

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