Iodine → HCID 21948202, compound

HRID 1839378Notes

Reaction equation

HRID 1839378 reaction equation
C([O-])([O-])=O.[K+].[K+].[I:7]I.[NH:9]([C:16]1[N:17]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:18]2[C:23]([C:24](=[O:26])[CH:25]=1)=[C:22]([CH3:27])[CH:21]=[C:20]([Cl:28])[N:19]=2)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[O-]S([O-])(=S)=O.[Na+].[Na+]>CN(C=O)C>[NH:9]([C:16]1[N:17]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:18]2[C:23]([C:24](=[O:26])[C:25]=1[I:7])=[C:22]([CH3:27])[CH:21]=[C:20]([Cl:28])[N:19]=2)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 807IodineHCID 11430Potassium CarbonateHCID 24477Sodium ThiosulfateHCID 21948152HCID 21948152, compound

Product 1

HCID 21948202HCID 21948202, compoundYield 56.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

K2CO3 (210 mg, 1.52 mmol) and I2 (390 mg, 1.52 mmol,) were added to a solution 2-anilino-7-chloro-5-methyl-1-phenyl-1,8-naphthyridin-4(1H)-one (500 mg, 1.38 mmol) in DMF (10 mL). The mixture was stirred for 30 min and then poured into an aqueous solution of saturated Na2S2O3 (10 mL). The aqueous solution was extracted with EtOAc. The combined organic extracts were dried over MgSO4, and concentrated in vacuo. Silica gel flash chromatography of the residue using 4:1 to 1:1 Hex:EtOAc afforded 2-anilino-7-chloro-3-iodo-5-methyl-1-phenyl-1,8-naphthyridin-4(1H)-one (380 mg, 56%): LCMS RT: 3.45 min, MH+: 488.2, Rf=0.5 (2:1 Hex:EtOAc).

Workup

  1. extractionThe aqueous solution was extracted with EtOAc
  2. dry with materialThe combined organic extracts were dried over MgSO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-aa49112c436b460c8206f9dbac255f83
Source dataset
uspto-grants-2004_01
Patent number
US06677352B1

Reaction notes

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