HCID 82481672, compound → HCID 86687869, compound

HRID 538095Notes

Reaction equation

HRID 538095 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][CH:14]=1)[CH2:5][C:6]1[O:10][N:9]=[C:8]([CH3:11])[N:7]=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[N: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)[O:10][N:9]=1

Participants

5

Reactant 2

HCID 82481672HCID 82481672, compoundHCID 178451183HCID 178451183, compound

Product 1

HCID 86687869HCID 86687869, compoundYield 52.8%

Reagents, catalysts & solvents 2

HCID 178418851HCID 178418851, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 5-(3-bromobenzyl)-3-methyl-1,2,4-oxadiazole 1098 (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 0.300 g tert-butyl 2-(3-((3-methyl-1,2,4-oxadiazol-5-yl)methyl)phenyl)acetate 1099. 1H NMR 300 MHz CDCl3: δ 7.40-7.18 (m, 4H), 4.17 (s, 2H), 3.51 (s, 2H), 2.36 (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-20162a18d821436c8a857af4c2301598
Source dataset
uspto-grants-2014_10
Patent number
US08865718B2

Reaction notes

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