Iodine → 3-IODO-1H-PYRROLO[3,2-C]PYRIDINE

HRID 1753057Notes

Reaction equation

HRID 1753057 reaction equation
[NH:1]1[C:9]2[CH:8]=[CH:7][N:6]=[CH:5][C:4]=2[CH:3]=[CH:2]1.[OH-].[K+].[I:12]I.[OH-].[NH4+]>CN(C=O)C.O>[I:12][C:3]1[C:4]2[CH:5]=[N:6][CH:7]=[CH:8][C:9]=2[NH:1][CH:2]=1

Participants

7

Reactant 4

HCID 807IodineHCID 92205-AzaindoleHCID 14797Potassium HydroxideHCID 14923Ammonium Hydroxide

Product 1

HCID 116873853-IODO-1H-PYRROLO[3,2-C]PYRIDINEYield 81%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 1H-pyrrolo[3,2-c]pyridine (20 g, 170 mmol) in DMF (100 mL) was added KOH (33.2 g, 593 mmol) and the mixture was stirred for 10 minutes. A solution of iodine (47.3 g, 186 mmol) in DMF (100 mL) was added at 0° C., and the reaction allowed to warm to room temperature over 1.5 hours. The reaction was poured onto an aqueous solution of Na2S2O5 (17.2 g) and ammonium hydroxide (35%, 170 mL) in water (2.5 L). The resulting precipitate was filtered, washed with water and dried to afford the title compound (33.5 g, 81%).

Workup

  1. filtrationThe resulting precipitate was filtered
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-01af5dea613948158d269a60313bc812
Source dataset
uspto-grants-2015_10
Patent number
US09163021B2

Reaction notes

Loading…