HCID 82481670, compound → HCID 86687871, compound

HRID 1910475Notes

Reaction equation

HRID 1910475 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][CH:14]=1)[CH2:5][C:6]1[O:7][C:8]([CH3:11])=[N:9][N:10]=1.[Cl-].[C:16]([O:20][C:21](=[O:24])[CH2:22][Zn+])([CH3:19])([CH3:18])[CH3:17]>O1CCOCC1.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[CH3:11][C:8]1[O:7][C:6]([CH2:5][C:4]2[CH:3]=[C:2]([CH2:22][C:21]([O:20][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:24])[CH:14]=[CH:13][CH:12]=2)=[N:10][N:9]=1

Participants

5

Reactant 2

HCID 82481670HCID 82481670, compoundHCID 178451183HCID 178451183, compound

Product 1

HCID 86687871HCID 86687871, compoundYield 59.5%

Reagents, catalysts & solvents 2

HCID 178418851HCID 178418851, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-(3-bromobenzyl)-5-methyl-1,3,4-oxadiazole 1105 (0.50 g, 1.97 mmol) in dioxane (1 mL), under an atmosphere of Argon, was added Bis(tri-t-butylphosphine)palladium(0) (0.15 g, 0.295 mmol) followed by the addition of 2-tert-butoxy-2-oxoethylzinc chloride (0.5 M in diethyl ether, 4.92 mmol, 9.84 mL). The mixture was allowed to stir under Argon for 20 hours and the volatiles were removed under reduced pressure. The residue was taken up in EtOAc (10 mL) and washed with water (2×5 mL), brine (2×5 mL) and dried over Na2SO4. The Na2SO4 was removed by filtration and the volatiles removed under reduced pressure. The crude material was purified by normal phase chromatography 0-50% EtOAc/Hexanes to give 0.338 g of tert-butyl 2-(3-((5-methyl-1,3,4-oxadiazol-2-yl)methyl)phenyl)acetate 1106. 1H NMR 300 MHz CDCl3: δ 7.24 (m, 4H), 4.12 (s, 2H), 3.51 (s, 2H), 2.46 (s, 3H), 1.43 (s, 9H).

Workup

  1. customthe volatiles were removed under reduced pressure
  2. washwashed with water (2×5 mL), brine (2×5 mL)
  3. dry with materialdried over Na2SO4
  4. customThe Na2SO4 was removed by filtration
  5. customthe volatiles removed under reduced pressure
  6. customThe crude material was purified by normal phase chromatography 0-50% EtOAc/Hexanes

Sources & evidence

ORD record
ord-c8591b7f24494a42805c36710fc097ad
Source dataset
uspto-grants-2013_12
Patent number
US08604016B2

Reaction notes

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