Diiodomethane → 4-(5-Fluoro-4-iodo-2-methylphenyl)-2-methylpyridine

HRID 592211

Reaktionsgleichung

Reaktionsgleichung von HRID 592211
[F:1][C:2]1[CH:8]=[C:7]([C:9]2[CH:14]=[CH:13][N:12]=[C:11]([CH3:15])[CH:10]=2)[C:6]([CH3:16])=[CH:5][C:3]=1N.N(OCCC(C)C)=O.C(I)[I:26]>>[F:1][C:2]1[C:3]([I:26])=[CH:5][C:6]([CH3:16])=[C:7]([C:9]2[CH:14]=[CH:13][N:12]=[C:11]([CH3:15])[CH:10]=2)[CH:8]=1

Komponenten

4

Edukt 3

HCID 6346DiiodomethaneHCID 8053Isoamyl NitriteHCID 584477092-Fluoro-5-methyl-4-(2-methylpyridin-4-yl)aniline

Produkt 1

HCID 584479154-(5-Fluoro-4-iodo-2-methylphenyl)-2-methylpyridine

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To the solution of 2-fluoro-5-methyl-4-(2-methylpyridin-4-yl)aniline 191-3 (1.02 g, 4.7 mmol) in CH2I2 (16 mL) was added isoamyl nitrite (6 mL) slowly at −10° C. After 20 minutes, the reaction was heated to 100° C. for 2 hours. The solvent was removed by rotary evaporation and the residue was dissolved in ethyl acetate and washed with Na2S2O5, brine and taken to dryness by rotary evaporation. The residue was purified by silica gel flash chromatography, eluted with 40% ethyl acetate in hexane to give 4-(5-fluoro-4-iodo-2-methylphenyl)-2-methylpyridine 191-4. MS m/z 328.10 (M+1).

Aufarbeitung

  1. customThe solvent was removed by rotary evaporation
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with Na2S2O5, brine
  4. customtaken to dryness by rotary evaporation
  5. customThe residue was purified by silica gel flash chromatography
  6. washeluted with 40% ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-4fd18a37e17842a4a4c6b81003778c12
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09238646B2

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