Iodine chloride → HCID 90409982, compound

HRID 516564Notes

Reaction equation

HRID 516564 reaction equation
[I:1]Cl.[NH2:3][C:4]1[C:9]([F:10])=[C:8]([C:11]2[CH:16]=[CH:15][C:14]([Si](C)(C)C)=[CH:13][CH:12]=2)[N:7]=[C:6]([C:21]([O:23][CH3:24])=[O:22])[C:5]=1[Cl:25]>ClCCCl.S([O-])([O-])(=O)=S.[Na+].[Na+]>[NH2:3][C:4]1[C:9]([F:10])=[C:8]([C:11]2[CH:16]=[CH:15][C:14]([I:1])=[CH:13][CH:12]=2)[N:7]=[C:6]([C:21]([O:23][CH3:24])=[O:22])[C:5]=1[Cl:25]

Participants

5

Reactant 2

HCID 24640Iodine chlorideHCID 90409516HCID 90409516, compound

Product 1

HCID 90409982HCID 90409982, compoundYield 72.3%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 24477Sodium ThiosulfateSolvent

Conditions

Temperature
23 °C

Procedure

Iodine monochloride (280 mg, 1.7 mmol, 2.0 equiv) was added to a stirred solution of methyl 4-amino-3-chloro-5-fluoro-6-(4-(trimethylsilyl)phenyl)picolinate (300 mg, 0.85 mmol, 1.0 equiv) in 1,2-dichloroethane (5.7 mL) at 23° C. The resulting brown solution was stirred at 23° C. for 17 h. The reaction mixture was diluted with saturated solution of sodium thiosulfate (100 mL) and extracted with dichloromethane (4×40 mL). The combined organic layers were dried (magnesium sulfate), gravity filtered, and concentrated by rotary evaporation. The residue was purified by silica gel column chromatography (33% ethyl acetate in hexanes) to afford the title compound as a pale purple powder (250 mg, 71%).

Workup

  1. extractionextracted with dichloromethane (4×40 mL)
  2. dry with materialThe combined organic layers were dried (magnesium sulfate), gravity
  3. filtrationfiltered
  4. concentrationconcentrated by rotary evaporation
  5. customThe residue was purified by silica gel column chromatography (33% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-4f774624b42e4307b4ba1581378801c3
Source dataset
uspto-grants-2015_08
Patent number
US09113629B2

Reaction notes

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