HCID 2765836, compound → HCID 68195065, compound

HRID 2370638Notes

Reaction equation

HRID 2370638 reaction equation
Br[C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[N:11]1[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]1.[CH2:18]([Sn](CCCC)(CCCC)C(C)=C)[CH2:19][CH2:20]C>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:17][N:14]1[CH2:15][CH2:16][N:11]([C:3]2[CH:4]=[CH:5][C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=2[C:19]([CH3:20])=[CH2:18])[CH2:12][CH2:13]1

Participants

5

Reactant 2

HCID 2765836HCID 2765836, compoundHCID 10871254Stannane, tributyl(1-methylethenyl)-

Product 1

HCID 68195065HCID 68195065, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
105 °C

Procedure

A mixture of 1-(2-bromo-4-nitrophenyl)-4-methylpiperazine (0.810 g, 2.70 mmol), tetrakis(triphenylphosphine)palladium(0) (0.094 g, 0.081 mmol), and tributyl(prop-1-en-2-yl)stannane (0.983 g, 2.97 mmol) in 1,4-dioxane (30 mL) was degassed and heated at 105° C. overnight. After cooling, the suspension was filtered, concentrated, and purified on a 40 g column using the ISCO Companion flash system eluting with methanol/ethyl acetate (5:95 to 10:90) to provide the title compound.

Workup

  1. customwas degassed
  2. temperatureAfter cooling
  3. filtrationthe suspension was filtered
  4. concentrationconcentrated
  5. custompurified on a 40 g column
  6. washeluting with methanol/ethyl acetate (5:95 to 10:90)

Sources & evidence

ORD record
ord-3ecc0dbb731b4f16b30c0aadd8da55e5
Source dataset
uspto-grants-2014_04
Patent number
US08710065B2

Reaction notes

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