Methyl cyanoacetate → HCID 67288378, compound

HRID 1626474Notes

Reaction equation

HRID 1626474 reaction equation
[H-].[Na+].[C:3]([CH2:5][C:6]([O:8][CH3:9])=[O:7])#[N:4].Br[C:11]1[C:16]([Cl:17])=[CH:15][C:14]([Cl:18])=[CH:13][N:12]=1>CN1C(=O)CCC1>[C:3]([CH:5]([C:11]1[C:16]([Cl:17])=[CH:15][C:14]([Cl:18])=[CH:13][N:12]=1)[C:6]([O:8][CH3:9])=[O:7])#[N:4]

Participants

5

Reactant 3

HCID 7747Methyl cyanoacetateHCID 24758Sodium hydrideHCID 8170902-Bromo-3,5-dichloropyridine

Product 1

HCID 67288378HCID 67288378, compoundYield 21.7%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
0 °C

Procedure

NMP (7 mL) was added to a round bottom, placed under nitrogen and cooled to 0° C. NaH (1.16 g, 29.1 mmol) was added portionwise followed by the addition of methyl cyanoacetate (1.31 ml, 14.5 mmol) (in 3 mL of NMP) dropwise. After stirring for 30 minutes at 0° C., 2-bromo-3,5-dichloropyridine (3.0 g, 13.2 mmol) was added and the reaction was heated to 130° C. for 5 hours. The reaction was allowed to cool, poured into ice and extracted twice with ethyl acetate. The ethyl acetate was combined, dried over MgSO4, filtered and concentrated. The amorphous material was crystallized from methanol to afford the desired compound (700 mg, 2.86 mmol, 21.6% yield) as light brown needles.

Workup

  1. temperaturethe reaction was heated to 130° C. for 5 hours
  2. temperatureto cool
  3. additionpoured into ice
  4. extractionextracted twice with ethyl acetate
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe amorphous material was crystallized from methanol

Sources & evidence

ORD record
ord-8c5a2f96611c476297bf407e10e1799e
Source dataset
uspto-grants-2014_07
Patent number
US08785445B2

Reaction notes

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