Triethyl phosphite → HCID 21065007, compound

HRID 1243649Notes

Reaction equation

HRID 1243649 reaction equation
I[C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=1)=[O:11].[CH2:23]([O:25][P:26]([O:30]CC)[O:27][CH2:28][CH3:29])[CH3:24]>Cl[Pd]Cl>[CH2:23]([O:25][P:26]([C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=1)=[O:11])([O:27][CH2:28][CH3:29])=[O:30])[CH3:24]

Participants

4

Reactant 2

HCID 31215Triethyl phosphiteHCID 21930308HCID 21930308, compound

Product 1

HCID 21065007HCID 21065007, compoundYield 61.3%

Reagents, catalysts & solvents 1

HCID 24290Palladium ChlorideCatalyst

Conditions

Temperature
130 °C

Procedure

To a 30 mL vial, 1-(2-iodo-4-bromophenyl)-3-(3-trifluoromethylphenyl)urea (2.00 g, 4.12 mmol) was added along with triethylphosphite (1.03 g, 6.0 mmol) and PdCl2 (49 mg, 0.278 mmol). The vial was flushed with N2 sealed and then heated at 130° C. while stirring overnight. The resulting solution was cooled to room temperature, dissolved in a 1:1 mixture of EtOAc/hexane and then purified on a silica column using mixtures of EtOAc/hexanes to give 1.25 g of 1-(2-diethylphosphono-4-bromophenyl)-3-(3-trifluoromethylphenyl)urea as a white solid.

Workup

  1. customThe vial was flushed with N2
  2. customsealed
  3. temperatureThe resulting solution was cooled to room temperature
  4. dissolutiondissolved in a 1:1 mixture of EtOAc/hexane
  5. custompurified on a silica column

Sources & evidence

ORD record
ord-36f93446ec844d54a871e989cf5fc394
Source dataset
uspto-grants-2006_10
Patent number
US07119120B2

Reaction notes

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