Potassium Iodide → HCID 178489173, compound

HRID 917563Notes

Reaction equation

HRID 917563 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:26]=[C:27]([OH:29])[CH:28]=1)[CH2:5][NH:6][C:7]([NH2:25])=[N:8][C:9]([C:11]1[C:12]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)=[N:13][O:14][C:15]=1[CH3:16])=[O:10].Br[CH2:31][CH2:32][Cl:33].C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+]>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:26]=[C:27]([O:29][CH2:31][CH2:32][Cl:33])[CH:28]=1)[CH2:5][NH:6]/[C:7](/[NH2:25])=[N:8]/[C:9]([C:11]1[C:12]([C:17]2[CH:18]=[CH:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=2)=[N:13][O:14][C:15]=1[CH3:16])=[O:10]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 78491-Bromo-2-ChloroethaneHCID 10796Cesium carbonateHCID 178489174HCID 178489174, compound

Product 1

HCID 178489173HCID 178489173, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The compound of Example 23 (8.3 mg, 0.020 mmol), 1-bromo-2-chloroethane (14 mg, 0.1 mmol), cesium carbonate (13 mg, 0.04 mmol) and potassium iodide (4 mg, 0.024 mmol) were mixed in 1 mL of THF in an 8-mL glass vial. The vial was capped and shaken at RT overnight. The reaction mixture was filtered through Acrodisc Syringe Filter (0.45 μm). Solvent was evaporated in vacuo. The residue was purified by preparative HPLC to give 2.2 mg of the title compound. LC/MS (method A) RT 2.61, MH+ 477. 1H NMR (500 MHz, CD3OD) δ 7.60 (d, J=8.2 Hz, 2H), 7.05 (d, J=8.2 Hz, 2H), 6.99 (s, 2H), 6.90 (s, 1 H), 4.53 (s, 2 H), 4.26 (t, J=5.3 Hz, 2 H), 3.86 (t, J=5.3 Hz, 2 H), 3.84 (s, 3 H), 2.66 (s, 3 H).

Workup

  1. customThe vial was capped
  2. filtrationThe reaction mixture was filtered through Acrodisc Syringe
  3. filtrationFilter (0.45 μm)
  4. customSolvent was evaporated in vacuo
  5. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-b5e8961abdaa401398f234ffe09cec33
Source dataset
uspto-grants-2007_09
Patent number
US07273882B2

Reaction notes

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