Diisopropylethylamine → HCID 21959524, compound

HRID 887652Notes

Reaction equation

HRID 887652 reaction equation
Br[C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[C:11]([C:14]1[CH2:15][CH2:16][N:17]([CH3:20])[CH2:18][CH:19]=1)([CH3:13])[CH3:12].CCN(C(C)C)C(C)C>CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:20][N:17]1[CH2:16][C:15]2[C:4]3[C:3](=[CH:2][CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=3)[C:11]([CH3:13])([CH3:12])[C:14]=2[CH:19]=[CH:18]1

Participants

5

Reactant 2

HCID 81531DiisopropylethylamineHCID 21959640HCID 21959640, compound

Product 1

HCID 21959524HCID 21959524, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

4-[1-(2-Bromo-4-nitro-phenyl)-1-methyl-ethyl]-1-methyl-1,2,3,6-tetrahydro-pyridine (9 g), Pd(OAc)2 (900 mg), and DIEA (15 mL) was dissolved in DMF (300 mL), and heated to 80° C. overnight. Solvents were removed in vacuo. The residue was partitioned between CH2Cl2/NaHCO3(sat, aq.). The CH2Cl2 layer was washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified via flash chromatography on silica to give the desired compound. (MS: M+H=257)

Workup

  1. customSolvents were removed in vacuo
  2. customThe residue was partitioned between CH2Cl2/NaHCO3(sat, aq.)
  3. washThe CH2Cl2 layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified via flash chromatography on silica

Sources & evidence

ORD record
ord-85cb4d4636a647e9b41634aa4b6bbcdc
Source dataset
uspto-grants-2012_08
Patent number
US08247430B2

Reaction notes

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