4-Iodo-1-tritylimidazole → HCID 22186119, compound

HRID 1837518Notes

Reaction equation

HRID 1837518 reaction equation
C([Mg]Br)C.I[C:6]1[N:7]=[CH:8][N:9]([C:11]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:10]=1.[N+:30]([C:33]1[CH:34]=[CH:35][CH:36]2[CH:41]([CH:42]=1)[C:40](OS(C(F)(F)F)(=O)=O)=[CH:39][CH2:38][CH2:37]2)([O-:32])=[O:31]>O1CCCC1.C(OCC)C.[Cl-].[Zn+2].[Cl-].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd]>[N+:30]([C:33]1[CH:34]=[CH:35][CH:36]2[CH:41]([CH:42]=1)[C:40]([C:6]1[N:7]=[CH:8][N:9]([C:11]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:10]=1)=[CH:39][CH2:38][CH2:37]2)([O-:32])=[O:31]

Participants

8

Reactant 3

HCID 6182524-Iodo-1-tritylimidazoleHCID 87898979HCID 87898979, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 22186119HCID 22186119, compound

Reagents, catalysts & solvents 4

HCID 3007855ZincchlorideCatalystHCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

At ambient temperature, 15.34 ml of 3M ethylmagnesium bromide are poured into 16.74 g of 4-iodo-1-trityl-1H-imidazole dissolved in 250 ml of tetrahydrofuran. After 1 hour, 76.6 ml of a 1N solution of zinc chloride in diethyl ether are poured in. After contact for 1 hour, 12.4 g of the product obtained in Step 1 dissolved in 100 ml of tetrahydrofuran and 2.22 g of tetrakis(triphenylphosphine)palladium(O) are added and the whole is heated at reflux. Following hydrolysis with a saturated solution of ammonium chloride and extraction with dichloromethane, the organic phase is washed with water. The solvent is then evaporated off and the residue is purified by chromatography on silica gel using as eluant an 80/20 cyclohexane/ethyl acetate mixture.

Workup

  1. waitAfter contact for 1 hour
  2. temperaturethe whole is heated
  3. temperatureat reflux
  4. customhydrolysis
  5. extractionwith a saturated solution of ammonium chloride and extraction with dichloromethane
  6. washthe organic phase is washed with water
  7. customThe solvent is then evaporated off
  8. customthe residue is purified by chromatography on silica gel using as eluant an 80/20 cyclohexane/ethyl acetate mixture

Sources & evidence

ORD record
ord-4b4ffc6c1dde45a5995c212d8900906e
Source dataset
uspto-grants-2004_08
Patent number
US06784183B2

Reaction notes

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