Diiodomethane → HCID 59370288, compound

HRID 705098Notes

Reaction equation

HRID 705098 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-7234dd5dea5b42448cea9daf0bdd778a
Source dataset
uspto-grants-2015_11
Patent number
US09173861B2

Reaction notes

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