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

HRID 2114047Notes

Reaction equation

HRID 2114047 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[CH:15]=[C:16]2[CH:22]=[CH:21][NH:20][C:17]2=[N:18][CH:19]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].[I:25]I>CN(C=O)C>[I:25][C:22]1[C:16]2[C:17](=[N:18][CH:19]=[C:14]([C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=3[O:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:15]=2)[NH:20][CH:21]=1

Participants

5

Reactant 3

HCID 807IodineHCID 14797Potassium HydroxideHCID 578301595-(2-Phenoxy-phenyl)-1h-pyrrolo[2,3-b]pyridine

Product 1

HCID 598119243-Iodo-5-(2-phenoxy-phenyl)-1H-pyrrolo[2,3-b]pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the azaindole 25 (18.30 g, 63.9 mmol) in DMF (100 mL) was added KOH (13.27 g, 236.5 mmol) in a single portion. After 0.5 h, iodine (16.18 g, 63.9 mmol) was added in portions over a 3 min. period. After a further 1 h the reaction was quenched by the addition of a solution of sodium thiosulfate (70 g) in H2O (400 mL). The semisolid was filtered off, dissolved in dichloromethane. The solution and washed with saturated brine (1×), dried (MgSO4), and concentrated to afford the iodide 26, which was used directly in the next step without further purification. 1H NMR (400 MHz; CDCl3) δ6.92-6.95 (m, 2H), 7.01 (tt, J=7.3, 1.0 Hz, 1H), 7.08 (dd, J=8.1, 1.3 Hz, 1H), 7.23-7.30 (m, 3H), 7.36 (dt, J=7.3, 1.8 Hz, 1H), 7.40 (s, H), 7.54 (dd, J=7.6, 1.8 Hz, 1H), 7.93 (d, J=2.0 Hz, 1H), 8.54 (d, J=2.0 Hz, 1H) and 11.06 (bs, 1H).

Workup

  1. customAfter a further 1 h the reaction was quenched by the addition of a solution of sodium thiosulfate (70 g) in H2O (400 mL)
  2. filtrationThe semisolid was filtered off
  3. dissolutiondissolved in dichloromethane
  4. washThe solution and washed with saturated brine (1×)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-cd5d5abb3d7d4067acf955a23a372970
Source dataset
uspto-grants-2008_10
Patent number
US07432375B2

Reaction notes

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