N-methyl-2-pyrrolidone → HCID 71239552, compound

HRID 1508178Notes

Reaction equation

HRID 1508178 reaction equation
[CH3:1][O:2][C:3](=[O:14])[CH2:4][C:5]1[C:10](I)=[CH:9][C:8]([Cl:12])=[CH:7][C:6]=1[Cl:13].[CH3:15][N:16]1C(=O)CCC1>[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>[CH3:1][O:2][C:3](=[O:14])[CH2:4][C:5]1[C:10]([C:15]#[N:16])=[CH:9][C:8]([Cl:12])=[CH:7][C:6]=1[Cl:13]

Participants

5

Reactant 2

HCID 13387N-methyl-2-pyrrolidoneHCID 71239338HCID 71239338, compound

Product 1

HCID 71239552HCID 71239552, compound

Reagents, catalysts & solvents 2

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

Conditions

Temperature
110 °C

Procedure

A mixture of 2,4-dichloro-6-iodophenylacetic acid methyl ester (0.95 mmol), Zn(CN)2 (0.95 mmol) and tetrakis(triphenylphosphine)palladium (0.05 mmol) in 1.5 mL anhydrous NMP was degassed and heated under argon in a closed vial to 110° C. for 2.5 h. The reaction mixture was cooled to RT, quenched with 10% aq Na2CO3 solution and extracted with EtOAc (3×). The combined organic layers were dried over MgSO4 and concentrated in vacuo. Purification by CC using Hept/EtOAc (9/1) gives the desired product as yellow oil.

Workup

  1. customwas degassed
  2. temperatureThe reaction mixture was cooled to RT
  3. customquenched with 10% aq Na2CO3 solution
  4. extractionextracted with EtOAc (3×)
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customPurification by CC

Sources & evidence

ORD record
ord-0d358e175e5840a28a62bee16433638c
Source dataset
uspto-grants-2015_12
Patent number
US09221832B2

Reaction notes

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