Iodine → 3-Iodo-5-(phenylsulfanyl)-1H-pyrrolo[2,3-b]pyridine

HRID 1991094Notes

Reaction equation

HRID 1991094 reaction equation
[C:1]1([S:7][C:8]2[CH:9]=[C:10]3[CH:16]=[CH:15][NH:14][C:11]3=[N:12][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[K+].[I:19]I.[O-]S([O-])(=S)=O.[Na+].[Na+]>CN(C=O)C.O>[I:19][C:16]1[C:10]2[C:11](=[N:12][CH:13]=[C:8]([S:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH:9]=2)[NH:14][CH:15]=1

Participants

7

Reactant 4

HCID 807IodineHCID 14797Potassium HydroxideHCID 24477Sodium ThiosulfateHCID 591287095-(Phenylsulfanyl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 591287053-Iodo-5-(phenylsulfanyl)-1H-pyrrolo[2,3-b]pyridineYield 98%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2 (135 mg, 0.60 mmol) in DMF (1.5 mL) was added solid KOH (124 mg, 2.21 mmol) and the reaction mixture stirred for 20 min. Iodine (167 mg, 0.66 mmol) was then added and the stirring continued for 40 min. A mixture of water (8.8 mL) and sat. aq. Na2S2O3 (1.3 mL) was added rapidly, and the resulting solid filtered off, washed with water (2×) and dried in vacuum to give iodide 3 as a creamy solid (205 mg, 98%); 1H NMR (400 MHz, CDCl3+2 drops CD3OD) δ 7.10-7.30 (m, 5H), 7.45 (s, 1H), 7.94 (d, J=2.0 Hz, 1H), 8.35 (d, J=1.9 Hz, 1H).

Workup

  1. waitthe stirring continued for 40 min
  2. additionwas added rapidly
  3. filtrationthe resulting solid filtered off
  4. washwashed with water (2×)
  5. customdried in vacuum

Sources & evidence

ORD record
ord-333e844165204f2bb43227c41999f2f3
Source dataset
uspto-grants-2010_01
Patent number
US07645769B2

Reaction notes

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