Diiodomethane → N-(5-Iodo-4-methylpyridin-2-yl)-2,2-dimethylpropanamide

HRID 1740937Notes

Reaction equation

HRID 1740937 reaction equation
N[C:2]1[C:3]([CH3:15])=[CH:4][C:5]([NH:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])=[N:6][CH:7]=1.N(OCCC(C)C)=O.[I:24]CI>>[I:24][C:2]1[C:3]([CH3:15])=[CH:4][C:5]([NH:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])=[N:6][CH:7]=1

Participants

4

Reactant 3

HCID 6346DiiodomethaneHCID 8053Isoamyl NitriteHCID 21834443HCID 21834443, compound

Product 1

HCID 17750196N-(5-Iodo-4-methylpyridin-2-yl)-2,2-dimethylpropanamide

Conditions

Temperature
85 °C

Procedure

A mixture of 5-amino-4-methyl-2-(trimethylacetyl)aminopyridine (1.0 g, 4.82 mmol) in 34 mL of diiodomethane containing isoamyl nitrite (4.0 mL, 29.77 mmol) was heated at 85° C. for 0.5 h, cooled to room temperature and evaporated at 60° C. under high vacuum to give a red semi-solid. The crude material was purified by silica gel column chromatography using 10% ether/hexane as eluant to give the title compound.

Workup

  1. temperaturecooled to room temperature
  2. customevaporated at 60° C. under high vacuum
  3. customto give a red semi-solid
  4. customThe crude material was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a0e2610d2ad04d08ba9aec218cb9afc8
Source dataset
uspto-grants-1999_10
Patent number
US05972975

Reaction notes

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