2-(Dimethylamino)ethanol → HCID 84649317, compound

HRID 1908665Notes

Reaction equation

HRID 1908665 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.[CH2:11]([Zn]CC)[CH3:12].CCCCCC.CN(CCO)C>C1COCC1.Cl[Pd]Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH2:11]([C:2]1[N:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1)[CH3:12]

Participants

7

Reactant 4

HCID 79022-(Dimethylamino)ethanolHCID 8058HexaneHCID 27796981-(6-Chloropyridin-3-yl)ethan-1-oneHCID 178418750HCID 178418750, compound

Product 1

HCID 84649317HCID 84649317, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 8028TetrahydrofuranSolvent

Procedure

A dry round bottomed flask was charged with 1-(6-chloro-3-pyridinyl)-1-ethanone (IM15) (3.596 g, 23.11 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]-dichloropalladium(II) (1.694 g, 2.315 mmol) in THF (100 mL) under N2. A 1 M solution of diethyl zinc in hexane (35 mL, 35 mmol) was added drop wise to this mixture followed by N,N-dimethylaminoethanol (0.50 mL, 5.0 mmol). The mixture was heated to reflux for 30 minutes. The mixture was cooled to room temperature and then quenched by the addition of saturated aqueous NH4Cl solution (100 mL). The mixture was filtered through a plug of celite. The aqueous layer was extracted with EtOAc (3×100 mL). The combined organic layers were washed with water, brine and then dried over Mg2SO4. Flash Chromatography (120 g silica, 0-40% EtOAc in heptanes) gave the title compound as a yellow oil (0.699 g, 20%) sufficiently pure for the next step.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 30 minutes
  3. customquenched by the addition of saturated aqueous NH4Cl solution (100 mL)
  4. filtrationThe mixture was filtered through a plug of celite
  5. extractionThe aqueous layer was extracted with EtOAc (3×100 mL)
  6. washThe combined organic layers were washed with water, brine
  7. dry with materialdried over Mg2SO4

Sources & evidence

ORD record
ord-599dcb88797d48f1b6677a7d8f80399f
Source dataset
uspto-grants-2013_12
Patent number
US08598213B2

Reaction notes

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