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Iodine → Benzyl 5-(3-iodo-4-methoxyphenyl)-6-methylpyridine-2-carboxylate

HRID 607072
Notes
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Reaction equation

HRID 607072 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[CH:11][C:12]([C:16]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:17])=[N:13][C:14]=2[CH3:15])=[CH:5][CH:4]=1.[I:26]I>CO.S([O-])([O-])(=O)=O.[Ag+2]>[I:26][C:8]1[CH:7]=[C:6]([C:9]2[CH:10]=[CH:11][C:12]([C:16]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:17])=[N:13][C:14]=2[CH3:15])[CH:5]=[CH:4][C:3]=1[O:2][CH3:1]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 807Iodine2×HCID 57704814Benzyl 5-(4-methoxyphenyl)-6-methylpyridine-2-carboxylate

Product 1

HCID 57704790Benzyl 5-(3-iodo-4-methoxyphenyl)-6-methylpyridine-2-carboxylate

Reagents, catalysts & solvents 2

HCID 178418844HCID 178418844, compoundCatalyst2×HCID 887MethanolSolvent

Procedure

Benzyl 5-(4-methoxyphenyl)-6-methylpyridine-2-carboxylate (150 mg, 0.45 mmol), iodine (228 mg, 0.898 mmol), silver sulfate (402 mg, 1.29 mmol) were stirred in methanol (3 mL) at room temperature overnight. More iodine (57 mg, 0.22 mmol) and silver sulfate (100 mg, 0.32 mmol) were added into reaction mixture after 25 hours. Added aqueous NaHSO3 solution (sat., 20 mL) into the reaction mixture after additional 1.5 hours to quench the reaction. The reaction mixture was extracted with ethyl acetate. The combined extracts were dried over Na2SO4 followed by filtration and concentration to afford a clear oil. The crude oil was purified by preparative TLC on SiO2 (eluted with 30% ethyl acetate in hexanes) to afford benzyl 5-(3-iodo-4-methoxyphenyl)-6-methylpyridine-2-carboxylate. LCMS calc.=459.03; found=460.17 (M+1)+.

Workup

  1. customAdded aqueous NaHSO3 solution (sat., 20 mL) into the reaction mixture after additional 1.5 hours to quench
  2. customthe reaction
  3. extractionThe reaction mixture was extracted with ethyl acetate
  4. dry with materialThe combined extracts were dried over Na2SO4
  5. filtrationfollowed by filtration and concentration
  6. customto afford a clear oil
  7. customThe crude oil was purified by preparative TLC on SiO2 (eluted with 30% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-f98947ce021f48c097610ef4fef6f949
Source dataset
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07915271B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes