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

HRID 592211

Reaction equation

HRID 592211 reaction equation
[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

Participants

4

Reactant 3

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

Product 1

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

Conditions

Temperature
100 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-4fd18a37e17842a4a4c6b81003778c12
Source dataset
uspto-grants-2016_01
Patent number
US09238646B2

Linked notes

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