Iodine → HCID 67959670, compound

HRID 1529293Notes

Reaction equation

HRID 1529293 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[CH:12]2.[I:18]I.[OH-].[K+].S(=O)(O)[O-].[Na+]>CN(C=O)C>[F:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[C:3]=1[C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[C:12]2[I:18]

Participants

6

Reactant 4

HCID 807IodineHCID 14797Potassium HydroxideHCID 23665763Sodium BisulfiteHCID 67958183HCID 67958183, compound

Product 1

HCID 67959670HCID 67959670, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-(2,6-difluorophenyl)-1H-indole (1.06 g, 4.62 mmol) in DMF (10 mL) was added I2 (0.262 mL, 5.09 mmol) followed by KOH (0.317 mL, 11.56 mmol). The reaction was stirred at RT for 1 h, and then poured into ice/water mixture with sodium bisulfite. The mixture was extracted with DCM and the combined organic layers were washed with water, brine, dried over Na2SO4, filtered and concentrated to give the crude product. MS (ESI, pos. ion) m/z: 355.0 (M+1).

Workup

  1. extractionThe mixture was extracted with DCM
  2. washthe combined organic layers were washed with water, brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-315d14ef8af949c790fb906744b21936
Source dataset
uspto-grants-2015_07
Patent number
US09090593B2

Reaction notes

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