Potassium Iodide → HCID 66590888, compound

HRID 2264659Notes

Reaction equation

HRID 2264659 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][N:10]([CH2:16][C:17]2[O:18][CH:19]=[CH:20][CH:21]=2)[CH2:11][C:12]([NH:14][CH3:15])=[O:13])[CH:5]=[CH:6][CH:7]=1.[Cl:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[F:30].C([O-])([O-])=O.[K+].[K+].[I-].[K+]>CN(C)C=O>[ClH:22].[F:30][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[CH2:23][O:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][N:10]([CH2:16][C:17]2[O:18][CH:19]=[CH:20][CH:21]=2)[CH2:11][C:12]([NH:14][CH3:15])=[O:13])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 9580Benzene, 1-(chloromethyl)-2-fluoro-HCID 11430Potassium CarbonateHCID 59596834HCID 59596834, compound

Product 1

HCID 66590888HCID 66590888, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 60 mg (0.21 mmol) of 2-[[2-(3-hydroxy-phenyl)-ethyl]-(furan-2-ylmethyl)amino]-N-methyl-acetamide, 36 mg (0.25 mmol) of 1-chloromethyl-2-fluoro-benzene, 44 mg of K2CO3 (0.32 mmol) and 3 mg of potassium iodide in 4 ml of dimethylformamide was refluxed overnight. The solvent was removed under vacuum and the crude product was purified by preparative HPLC. The isolated product was dissolved in ethyl acetate/hydrochloric acid. The solvent was removed under vacuum and the residue was triturated with diethyl ether. 65 mg (72% yield) of the title compound were isolated as a white solid.

Workup

  1. customThe solvent was removed under vacuum
  2. customthe crude product was purified by preparative HPLC
  3. dissolutionThe isolated product was dissolved in ethyl acetate/hydrochloric acid
  4. customThe solvent was removed under vacuum
  5. customthe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-7be894a24da446a9ae3fd25c859695f4
Source dataset
uspto-grants-2010_12
Patent number
US07855227B2

Reaction notes

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