Dimethylformamide → 5-(Methoxymethyl)picolinonitrile

HRID 627711Notes

Reaction equation

HRID 627711 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][O:9][CH3:10])=[CH:4][N:3]=1.[C:11]([Zn]C#N)#[N:12].CN(C=O)C>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.O>[CH3:10][O:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([C:11]#[N:12])=[N:3][CH:4]=1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 190109212-Chloro-5-(methoxymethyl)pyridineHCID 178514179HCID 178514179, compound

Product 1

HCID 669208935-(Methoxymethyl)picolinonitrileYield 70.4%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-chloro-5-(methoxymethyl)pyridine (0.831 g, 5.27 mmol), tetrakis (1.219 g, 1.055 mmol), dicyanozinc (0.929 g, 7.91 mmol) and DMF (17.58 ml) was stirred at 100° C. for 3 hrs. The reaction was treated with water and extracted with EtOAc. The organic portion was dried over Na2SO4, filtered, and concentrated in vacuo. The crude material was purified by column chromatography, eluting with 10-40% EtOAc/Heptanes to give the title compound (550 mg, 3.71 mmol, 70.4%). MS m/z=149.1 (M+H).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic portion was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude material was purified by column chromatography
  6. washeluting with 10-40% EtOAc/Heptanes

Sources & evidence

ORD record
ord-3a9abb77196a491189da3fdfd21c9a7b
Source dataset
uspto-grants-2016_04
Patent number
US09309263B2

Reaction notes

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