Iodine → HCID 90123714, compound

HRID 528847Notes

Reaction equation

HRID 528847 reaction equation
[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][C:8]([S:12]([NH2:15])(=[O:14])=[O:13])=[CH:9][CH:10]=2)[CH:5]=[CH:4]1)[CH3:2].[I:16]I.[OH-].[K+]>CN(C=O)C.CCOC(C)=O.OS([O-])=O.[Na+]>[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][C:8]([S:12]([NH2:15])(=[O:13])=[O:14])=[CH:9][CH:10]=2)[C:5]([I:16])=[CH:4]1)[CH3:2]

Participants

7

Reactant 3

HCID 807IodineHCID 14797Potassium HydroxideHCID 71062527HCID 71062527, compound2×

Product 1

HCID 90123714HCID 90123714, compoundYield 35%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolventHCID 23665763Sodium BisulfiteSolvent

Procedure

To a solution of 1-ethyl-1H-indole-5-sulfonamide (Intermediate 56, 175 mg, 0.78 mmol) in DMF (5.0 mL) was added a solution of iodine (218 mg, 0.86 mmol) in DMF (5.0 mL). KOH (109 mg, 1.95 mmol) was then added, and the resulting reaction mixture was stirred at room temperature for 24 h. The reaction mixture was then diluted with EtOAc and sat. aq. NaHSO3 solution. The organic layer was washed with sat. aq. NaCl solution, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by preparative HPLC to give the title compound (95 mg, 35%) as a pale yellow solid after lyophilization. 1H NMR (DMSO-d6) δ 7.86-7.76 (m, 2H), 7.74-7.61 (m, 2H), 7.21 (s, 2H), 4.28 (q, J=7.2 Hz, 2H), 1.36 (t, J=7.3 Hz, 3H); MS(ESI+) m/z 351.1 (M+H)+.

Workup

  1. customthe resulting reaction mixture
  2. washThe organic layer was washed with sat. aq. NaCl solution
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-0ee64618c8fc4fa5908c28c0d97c3a4e
Source dataset
uspto-grants-2016_05
Patent number
US09346795B2

Reaction notes

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