Iodine → 3-Iodo-1H-pyrrolo[2,3-b]pyridine-5-carbonitrile

HRID 2114056Notes

Reaction equation

HRID 2114056 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[C:8]([C:10]#[N:11])[CH:9]=[C:4]2[CH:3]=[CH:2]1.[OH-].[K+].[I:14]I.[O-]S([O-])(=S)=O.[Na+].[Na+]>CN(C=O)C.O>[I:14][C:3]1[C:4]2[C:5](=[N:6][CH:7]=[C:8]([C:10]#[N:11])[CH:9]=2)[NH:1][CH:2]=1

Participants

7

Reactant 4

HCID 807IodineHCID 14797Potassium HydroxideHCID 24477Sodium ThiosulfateHCID 117883551H-Pyrrolo[2,3-b]pyridine-5-carbonitrile

Product 1

HCID 242292213-Iodo-1H-pyrrolo[2,3-b]pyridine-5-carbonitrileYield 63.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 35 (3.0 g, 21.0 mmol) in DMF (53 mL) was added KOH (4.35 g, 77.5 mmol, pellets) and the reaction mixture stirred for 20 min., cooled to 0° C., and treated with iodine (5.32 g, 21.0 mmol). It was stirred at room temperature for 50 min then poured onto a mixture of water (306 mL)/sat. aqueous Na2S2O3 (46 mL). The resulting solid was filtered off and washed with water (2×) to give 36 (3.57 g, 63%) as creamy solid; 1H NMR (400 MHz, DMSO) δ 7.96 (s), 8.25 (s), 8.64 (s), 12.74 (NH).

Workup

  1. stirringIt was stirred at room temperature for 50 min
  2. filtrationThe resulting solid was filtered off
  3. washwashed with water (2×)

Sources & evidence

ORD record
ord-8173f2e7da534a8aa89cdf16b82091eb
Source dataset
uspto-grants-2008_10
Patent number
US07432375B2

Reaction notes

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