Iodine → HCID 71240245, compound

HRID 1403220Notes

Reaction equation

HRID 1403220 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[NH:12][C:11]([C:13]3[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=3[CH3:20])=[C:10]([C:21]([OH:23])=[O:22])[CH:9]=2)[CH:5]=[CH:4][N:3]=1.[I:24]I>CN(C=O)C.FC(F)(F)C([O-])=O.[Ag+]>[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[NH:12][C:11]([C:13]3[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=3[CH3:20])=[C:10]([C:21]([OH:23])=[O:22])[CH:9]=2)[C:5]([I:24])=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 807IodineHCID 70979820HCID 70979820, compound

Product 1

HCID 71240245HCID 71240245, compoundYield 81.6%

Reagents, catalysts & solvents 2

HCID 76299Silver trifluoroacetateCatalystHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
-40 °C

Procedure

5-(2-Amino-pyrimidin-4-yl)-2-(5-chloro-2-methyl-phenyl)-1H-pyrrole-3-carboxylic acid (0.70 g, 2.13 mmol) and Iodine (1.134 g, 4.47 mmol) in dry DMF (5 mL), under a nitrogen atmosphere, were stirred at −40° C. (internal temperature) and treated drop wise with silver trifluoroacetate (0.987 g, 4.47 mmol) in DMF (5 mL). The mixture was stirred at −40° C. for 7 h and then filtered over a short plug of celite. The panel was washed with DMF (5 mL) and the filtrate was collected in a flask containing 10% Na2S2O3 (50 mL). Precipitation of a pale yellow solid occurred. Dilution with water (50 mL) and filtration of the solid afforded 0.79 g of crude product, which was reacted in the next step with no further purification.

Workup

  1. filtrationfiltered over a short plug of celite
  2. washThe panel was washed with DMF (5 mL)
  3. customthe filtrate was collected in a flask
  4. additioncontaining 10% Na2S2O3 (50 mL)
  5. customPrecipitation of a pale yellow solid
  6. filtrationDilution with water (50 mL) and filtration of the solid

Sources & evidence

ORD record
ord-2f4569d0c97d463fbb33c0196e8c3bac
Source dataset
uspto-grants-2014_12
Patent number
US08912200B2

Reaction notes

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