Dimethylformamide → HCID 118235335, compound

HRID 59937Notes

Reaction equation

HRID 59937 reaction equation
Cl[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([F:9])=[CH:4][N:3]=1.[CH3:10][N:11](C=O)C>[C-]#N.[C-]#N.[Zn+2].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>[F:9][C:5]1[C:6]([CH3:8])=[CH:7][C:2]([C:10]#[N:11])=[N:3][CH:4]=1

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 269861742-Chloro-5-fluoro-4-methylpyridine

Product 1

HCID 118235335HCID 118235335, compound

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
150 °C

Procedure

A microwave tube was charged with 2-chloro-5-fluoro-4-methylpyridine (5.5 mmol), Zn(CN)2 (16.6 mmol), Pd(PPh3)4 (1.1 mmol) in DMF (20 mL). The mixture was stirred at 150° C. for 5 min in a microwave reactor. The mixture was combined with other crudes obtained following the procedure described above. The resulting mixture was filtered. The filtrate was concentrated under reduced pressure. The residue was diluted with EtOAc, washed (sat. NH4Cl), dried (Na2SO4) and concentrated. The residue was purified by flash column chromatography (SiO2, 5:95 to 15:85 EtOAc/petroleum ether) to yield the desired product.

Workup

  1. customobtained
  2. filtrationThe resulting mixture was filtered
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. additionThe residue was diluted with EtOAc
  5. washwashed (sat. NH4Cl)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. customThe residue was purified by flash column chromatography (SiO2, 5:95 to 15:85 EtOAc/petroleum ether)

Sources & evidence

ORD record
ord-f8460b3c1c6d4d2387629b1675226853
Source dataset
uspto-grants-2016_09
Patent number
US09440929B2

Reaction notes

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