Imidazole → HCID 89544426, compound

HRID 578871Notes

Reaction equation

HRID 578871 reaction equation
[Cl:1][C:2]1[C:3]([C:12]2([CH2:15]O)[CH2:14][CH2:13]2)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1.[I:41]I>ClCCl>[Cl:1][C:2]1[C:3]([C:12]2([CH2:15][I:41])[CH2:14][CH2:13]2)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 89544929HCID 89544929, compound

Product 1

HCID 89544426HCID 89544426, compoundYield 84.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

500 mg of [1-[3-chloro-5-(trifluoromethyl)-2-pyridyl]cyclopropyl]methanol (step 2) was dissolved in 20 ml dichloromethane and the solution was cooled in an ice bath. Then 560 mg triphenylphosphine and 150 mg imidazole were added. When a clear solution had formed, 550 mg iodine was added in portions. The reaction was stirred at ambient temperature overnight. The mixture was diluted with dichloromethane, washed with a saturated solution of sodium thiosulfate and the organic phase was concentrated. The residue was triturated with 30 ml of hexane. The solid was removed by filtration and the filtrate was concentrated. The residue was purified on 20 g of silica gel, eluent hexane/ethyl acetate (20:1). Thus, 610 mg of 3-chloro-2-[1-(iodomethyl)cyclopropyl]-5-(trifluoromethyl)pyridine was obtained as a pale yellow oil. 1H-NMR (CDCl3): 8.76 ppm (s, 1H), 7.93 ppm (s, 1H), 3.61 ppm (s, 2H), 1.49 ppm (m, 2H), 1.17 ppm (m, 2H).

Workup

  1. temperaturethe solution was cooled in an ice bath
  2. customWhen a clear solution had formed
  3. washwashed with a saturated solution of sodium thiosulfate
  4. concentrationthe organic phase was concentrated
  5. customThe residue was triturated with 30 ml of hexane
  6. customThe solid was removed by filtration
  7. concentrationthe filtrate was concentrated
  8. customThe residue was purified on 20 g of silica gel, eluent hexane/ethyl acetate (20:1)

Sources & evidence

ORD record
ord-2acdd7d6abbb4bdca67414a550075d43
Source dataset
uspto-grants-2015_05
Patent number
US09040708B2

Reaction notes

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