Diisopropylethylamine → 3-Tert-butyl-5-(2-chloro-5-iodophenyl)-1,2,4-oxadiazole

HRID 876638Notes

Reaction equation

HRID 876638 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][C:3]=1[C:4]([OH:6])=O.C(N(C(C)C)CC)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.O[NH:46][C:47](=[NH:52])[C:48]([CH3:51])([CH3:50])[CH3:49]>CN(C=O)C>[C:48]([C:47]1[N:52]=[C:4]([C:3]2[CH:7]=[C:8]([I:11])[CH:9]=[CH:10][C:2]=2[Cl:1])[O:6][N:46]=1)([CH3:51])([CH3:50])[CH3:49]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 5196382-Chloro-5-iodobenzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178446865HCID 178446865, compound

Product 1

HCID 582906973-Tert-butyl-5-(2-chloro-5-iodophenyl)-1,2,4-oxadiazoleYield 51.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-chloro-5-iodobenzoic acid (1.0 g, 3.54 mmol) in 40 mL DMF was added diisopropylethyl amine (1.23 mL, 7.08 mmol) followed by HATU (2.02 g, 5.31 mmol). After stirring the reaction at room temperature for 10 min, N-hydroxy-2,2-dimethylpropanimidamide (0.82 g, 7.08 mmol) was added. The resulting reaction mixture was stirred at room temperature for 1 h and then at 110° C. for 16 h. After cooling to room temperature the reaction was quenched with water and extracted with ethyl acetate. The combined organic fractions were washed with brine, dried (Na2SO4), concentrated, and purified by flash chromatography (2-5% EtOAc in hexanes) to yield 660 mg of intermediate US1-2.

Workup

  1. customthe reaction at room temperature for 10 min
  2. customThe resulting reaction mixture
  3. stirringwas stirred at room temperature for 1 h
  4. customwas quenched with water
  5. extractionextracted with ethyl acetate
  6. washThe combined organic fractions were washed with brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated
  9. custompurified by flash chromatography (2-5% EtOAc in hexanes)

Sources & evidence

ORD record
ord-10865fc1b9f548fca6dcafae82daac93
Source dataset
uspto-grants-2015_03
Patent number
US08987242B2

Reaction notes

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