Water → HCID 70983869, compound

HRID 338876Notes

Reaction equation

HRID 338876 reaction equation
Br[C:2]1[C:11]([O:12][CH:13]([CH3:15])[CH3:14])=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH3:16])=[N:9]2)=[CH:4][CH:3]=1.[C:17]([Zn]C#N)#[N:18].O.C(OCC)(=O)C>CC(N(C)C)=O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].ClCCl.[Zn]>[CH:13]([O:12][C:11]1[C:2]([C:17]#[N:18])=[CH:3][CH:4]=[C:5]2[C:10]=1[N:9]=[C:8]([CH3:16])[CH:7]=[CH:6]2)([CH3:15])[CH3:14]

Participants

8

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 70984179HCID 70984179, compoundHCID 178514179HCID 178514179, compound

Product 1

HCID 70983869HCID 70983869, compoundYield 140%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 178418807HCID 178418807, compoundCatalystHCID 31374DimethylacetamideSolvent

Procedure

A solution of 7-bromo-8-isopropoxy-2-methylquinoline (1.13 g, 4.03 mmol), PdCl2(dppf) dichloromethane adduct (0.165 g, 0.202 mmol), zinc (0.063 g, 0.97 mmol) and dicyanozinc (0.31 g, 2.62 mmol) in DMA (5 mL) was stirred at 100° C. for 18 hours. After cooling to ambient temperature, water (10 mL) and ethyl acetate (20 mL) were added. The organic layer was separated, washed with brine, dried (sodium sulfate), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (DCM) to give 8-isopropoxy-2-methylquinoline-7-carbonitrile (0.83 g, 91.1%) as a solid.

Workup

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography on silica gel (DCM)

Sources & evidence

ORD record
ord-5f155366eba54c30987195e8eda1540d
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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