Iodine → HCID 66596209, compound

HRID 634273Notes

Reaction equation

HRID 634273 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]#[N:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[OH-].[K+].[I:14]I.S(=O)(O)[O-].[Na+]>CN(C=O)C>[I:14][C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[C:6]([C:10]#[N:11])[CH:5]=2)[NH:1][CH:2]=1

Participants

6

Reactant 4

HCID 807IodineHCID 14797Potassium HydroxideHCID 27513Indole-5-carbonitrileHCID 23665763Sodium Bisulfite

Product 1

HCID 66596209HCID 66596209, compoundYield 94.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1H-indole-5-carbonitrile (1 g, 7.048 mmol) in DMF (10 mL) was added KOH pellets (1.15 g, 21.14 mmol), followed by I2 (3.57 g, 14.08 mmol) portionwise. The reaction was stirred for 1 h at RT. 10% aq sodium bisulphite solution (10 mL) was added to the mixture and an off-white solid precipitate was formed. The suspension was filtered and the solid was washed with H2O (10 mL) and dried under vacuum to give 3-iodo-1H-indole-5-carbonitrile (1.7 g, 94.5%) as an off white solid. 1H NMR (400 MHz, DMSO-d6): δ 12.18 (brs, 1H), 7.78 (s, 1H), 7.75 (d, J=1.2 Hz, 1H), 7.59 (dd, J=8.4, 0.4 Hz, 1H), 7.52 (dd, J=8.4, 1.6 Hz, 1H).

Workup

  1. customan off-white solid precipitate was formed
  2. filtrationThe suspension was filtered
  3. washthe solid was washed with H2O (10 mL)
  4. customdried under vacuum

Sources & evidence

ORD record
ord-2ef0aace974741ec958a5b2dada4ef17
Source dataset
uspto-grants-2016_04
Patent number
US09321756B2

Reaction notes

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