Potassium Acetate → HCID 86594830, compound

HRID 917246Notes

Reaction equation

HRID 917246 reaction equation
BrC1C=C([C:9]2[O:10][C:11]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[CH:16][CH:15]=3)=[N:12][N:13]=2)C=C(Br)C=1.B1(B2OC(C)(C)C(C)(C)O2)OC(C)(C)C(C)(C)O1.C([O-])(=O)C.[K+]>CS(C)=O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH2:21]([O:20][C:17]1[CH:16]=[CH:15][C:14]([C:11]2[O:10][CH:9]=[N:13][N:12]=2)=[CH:19][CH:18]=1)[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

Participants

6

Reactant 3

HCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 21982087HCID 21982087, compound

Product 1

HCID 86594830HCID 86594830, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

Following this general procedure 2-(3,5-Dibromophenyl)-5-[4-(octyloxy)phenyl]-1,3,4-oxadiazole, bis(pinacolato)diboron, potassium acetate, and [1,1′-bis(diphenylphosphino)-ferrocene]dichloropalladium (II) (complexed 1:1 with dichlormethane—Aldrich, 0.089 g, 0.1 mmoles) are reacted in DMSO under nitrogen at 80° C. for 18 hrs. After cooling, the reaction mixture is poured onto ice water, the aqueous layer extracted three times with methylene chloride, the combined organic fractions washed with brine, dried over magnesium sulfate, filtered through a thin silica bed, rotoevaporated to yield the desired 2-(3,5-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)) phenyl)-5-[4-(octyloxy)phenyl]-1,3,4-oxadiazole. These general methods can be used to prepare a wide range of arylene oxadiazole, triazole and thiadiazole diboronic ester intermediates useful in preparing compounds of Formula 1.

Workup

  1. temperatureAfter cooling
  2. additionthe reaction mixture is poured onto ice water
  3. extractionthe aqueous layer extracted three times with methylene chloride
  4. washthe combined organic fractions washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered through a thin silica bed

Sources & evidence

ORD record
ord-7d72fe6880984946bb4853cd45a7a2a8
Source dataset
uspto-grants-2007_09
Patent number
US07271406B2

Reaction notes

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