N-methyl-2-pyrrolidone → HCID 67003372, compound

HRID 2362645Notes

Reaction equation

HRID 2362645 reaction equation
[Cl:1][C:2]1[C:3]([C:22]2[S:26][C:25]([C:27]3([O:31][CH2:32][O:33][CH3:34])[CH2:30][CH2:29][CH2:28]3)=[N:24][CH:23]=2)=[C:4]2[CH:10]=[C:9](I)[N:8]([S:12]([C:15]3[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[C:5]2=[N:6][CH:7]=1.C(=O)(O)[O-].[Na+].[CH3:40][N:41]1CCCC1=O>[C-]#N.[Zn+2].[C-]#N.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>[Cl:1][C:2]1[C:3]([C:22]2[S:26][C:25]([C:27]3([O:31][CH2:32][O:33][CH3:34])[CH2:30][CH2:29][CH2:28]3)=[N:24][CH:23]=2)=[C:4]2[CH:10]=[C:9]([C:40]#[N:41])[N:8]([S:12]([C:15]3[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[C:5]2=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 516892Sodium BicarbonateHCID 67003444HCID 67003444, compound

Product 1

HCID 67003372HCID 67003372, compound

Reagents, catalysts & solvents 2

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

Conditions

Temperature
150 °C

Procedure

A nitrogen-sparged solution of Example 1F (0.2 g, 0.318 mmol) in 1-methyl-2-pyrrolidinone (4.5 mL) was treated with zinc cyanide (0.039 g, 0.333 mmol) and tetrakis(triphenylphosphine)palladium (0.022 g, 0.019 mmol). The reaction was heated at 150° C. for 20 minutes in a Biotage Initiator microwave reactor. The reaction was cooled to ambient temperature, treated with saturated aqueous sodium bicarbonate, and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous sodium sulfate, filtered, and concentrated. The concentrate was purified by flash chromatography on silica gel, eluting with a gradient of from 0% to 15% ethyl acetate in hexane, to provide the title compound. MS ESI(+) m/z 529.0 [M+H]+.

Workup

  1. temperatureThe reaction was cooled to ambient temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe concentrate was purified by flash chromatography on silica gel
  8. washeluting with a gradient of from 0% to 15% ethyl acetate in hexane

Sources & evidence

ORD record
ord-8337b419f1ad4db39732811e34834fbc
Source dataset
uspto-grants-2014_04
Patent number
US08691810B2

Reaction notes

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