N-methyl-2-pyrrolidone → HCID 88585512, compound

HRID 2206908Notes

Reaction equation

HRID 2206908 reaction equation
Br[C:2]1[C:3]([CH3:26])=[N:4][C:5]([N:8]2[CH2:12][CH2:11][C:10]([C:17]3[CH:22]=[C:21]([Cl:23])[C:20]([Cl:24])=[C:19]([Cl:25])[CH:18]=3)([C:13]([F:16])([F:15])[F:14])[CH2:9]2)=[CH:6][CH:7]=1.[Cu](C#N)[C:28]#[N:29].CN1CCCC1=O>C(OCC)(=O)C>[CH3:26][C:3]1[N:4]=[C:5]([N:8]2[CH2:12][CH2:11][C:10]([C:17]3[CH:22]=[C:21]([Cl:23])[C:20]([Cl:24])=[C:19]([Cl:25])[CH:18]=3)([C:13]([F:15])([F:14])[F:16])[CH2:9]2)[CH:6]=[CH:7][C:2]=1[C:28]#[N:29]

Participants

5

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 87158388HCID 87158388, compoundHCID 178418260HCID 178418260, compound

Product 1

HCID 88585512HCID 88585512, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
200 °C

Procedure

3-Bromo-2-methyl-6-[3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]-pyridine (3.3 g) and copper cyanide (I) (0.65 g) were added to N-methyl-2-pyrrolidinone (10 ml). The mixture was heated for 4 hours at 200° C. using a microwave reactor (trade name: INITIATOR™, manufactured by Biotage). Upon the completion of the reaction, the reaction mixture was diluted with ethyl acetate and the precipitate was filtered off through a short silica gel layer. The filtrate was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography to obtain 2-methyl-6-[3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]nicotinonitrile (1.1 g).

Workup

  1. customUpon the completion of the reaction
  2. filtrationthe precipitate was filtered off through a short silica gel layer
  3. distillationThe filtrate was distilled off under reduced pressure
  4. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-0c6fd4d7332d4ddcad189cf775b4bc6b
Source dataset
uspto-grants-2016_06
Patent number
US09375000B2

Reaction notes

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