Diiodomethane → HCID 59370288, compound

HRID 1642303Notes

Reaction equation

HRID 1642303 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[C:5]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][N:12]=2)[CH:8]=[C:7](N)[CH:6]=1)[CH3:2].N(OCCC(C)C)=O.C(I)[I:29]>C(#N)C>[CH2:1]([O:3][C:4](=[O:19])[C:5]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][N:12]=2)[CH:8]=[C:7]([I:29])[CH:6]=1)[CH3:2]

Participants

5

Reactant 3

HCID 6346DiiodomethaneHCID 8053Isoamyl NitriteHCID 59370286HCID 59370286, compound

Product 1

HCID 59370288HCID 59370288, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-Amino-5-(5-methyl-pyridin-2-yl)-benzoic acid ethyl ester (3.7 g, 14.45 mmol) was added to 50 mL of acetonitrile, and the mixture was stirred at room temperature. Isoamyl nitrite (9.7 mL, 72.27 mmol) was slowly added, followed by methylene iodide (7.0 mL, 86.7 mmol). The reaction mixture was slowly heated to 60° C. for 30 minutes, then cooled to room temperature. The reaction mixture was partitioned between water and ethyl acetate, and the organic phase was separated, washed with water and brine, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by liquid chromatography (30% to 100% methylene chloride/hexanes) to give 3-iodo-5-(5-methyl-pyridin-2-yl)-benzoic acid ethyl ester, MS (M+H)=368.

Workup

  1. temperatureThe reaction mixture was slowly heated to 60° C. for 30 minutes
  2. temperaturecooled to room temperature
  3. customThe reaction mixture was partitioned between water and ethyl acetate
  4. customthe organic phase was separated
  5. washwashed with water and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by liquid chromatography (30% to 100% methylene chloride/hexanes)

Sources & evidence

ORD record
ord-78a297b6ed04490e9a66e4516cb83b67
Source dataset
uspto-grants-2012_02
Patent number
US08119644B2

Reaction notes

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