HCID 117676185, compound → HCID 117676155, compound

HRID 1506886Notes

Reaction equation

HRID 1506886 reaction equation
Br[C:2]1[CH:7]=[C:6]([F:8])[C:5]([CH:9]([CH3:14])[C:10]([O:12][CH3:13])=[O:11])=[C:4]([F:15])[CH:3]=1.[CH3:16][Zn]C>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Br[Pd]Br>[F:8][C:6]1[CH:7]=[C:2]([CH3:16])[CH:3]=[C:4]([F:15])[C:5]=1[CH:9]([CH3:14])[C:10]([O:12][CH3:13])=[O:11]

Participants

5

Reactant 2

HCID 117676185HCID 117676185, compoundHCID 178477796HCID 178477796, compound

Product 1

HCID 117676155HCID 117676155, compoundYield 77.4%

Reagents, catalysts & solvents 2

HCID 11104744HCID 11104744, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

Compound (30b) (5.4 g, 19.3 mmol) and dimethyl zinc (2M-solution in toluene, 38.7 mL, 77.4 mmol), and a solution (40 mL) of trans-dibromobis(triphenylphosphine)palladium(II) [trans-Pd(PPh3)2Br2] (0.085 g, 5.6 mol %) in 1,4-dioxane (40 mL) were treated in the same manner as in (k) above. The obtained crude product was subjected to silica gel column chromatography and elution with an n-hexane/ethyl acetate (4:1) solution to give 3.2 g (77%) of compound (31b) as colorless oil.

Workup

  1. customThe obtained crude product
  2. washwas subjected to silica gel column chromatography and elution with an n-hexane/ethyl acetate (4:1) solution

Sources & evidence

ORD record
ord-87a892031af744e98d7835555cbe6ced
Source dataset
uspto-grants-2015_12
Patent number
US09221786B2

Reaction notes

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