Dimethylformamide → HCID 15893398, compound

HRID 1443401Notes

Reaction equation

HRID 1443401 reaction equation
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][C:10]([CH:13]2[NH:17][C:16](=[O:18])[CH2:15][CH2:14]2)=[CH:9][CH:8]=1)(=O)=O.[CH3:21][N:22](C=O)C>CCOC(C)=O.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.[C-]#N.[Zn+2].[C-]#N>[C:21]([C:7]1[CH:12]=[CH:11][C:10]([CH:13]2[NH:17][C:16](=[O:18])[CH2:15][CH2:14]2)=[CH:9][CH:8]=1)#[N:22]

Participants

6

Reactant 2

HCID 6228DimethylformamideHCID 219184384-(5-Oxopyrrolidin-2-yl)phenyl trifluoromethanesulfonate

Product 1

HCID 15893398HCID 15893398, compoundYield 100%

Reagents, catalysts & solvents 3

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 5-(4-trifluoromethanesulfonyloxyphenyl)-2-pyrrolidinone (2.45 g, 8.22 mmol), tetrakis(triphenylphosphine)palladium (475 mg, 0.41 mmol), and zinc cyanide (1.45 g, 12.3 mmol) in 10 mL of DMF was flushed with nitrogen three times and then stirred at 80° C. After 3 hr, the mixture was cooled down to rt, diluted with EtOAc (10 mL), and filtered through a cake of Celite. The solid was washed with EtOAc, and the filtrates were combined and concentrated. Chromatography on a Biotage 40+M cartridge using 9:1 v/v EtOAc/CH3OH as the eluant gave 2.68 g (100%) of the title compound containing trace amount of DMF: 1H NMR (CD3OD) δ 1.90-1.97 (m, 1H), 2.43-2.51 (m, 2H), 2.60-2.67 (m, 1H), 4.85 (t, J=7.2, 1H), 7.41 (d, J=8.8, 2H), 7.65 (d, J=8.5, 2H).

Workup

  1. temperaturethe mixture was cooled down to rt
  2. filtrationfiltered through a cake of Celite
  3. washThe solid was washed with EtOAc
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8ec1de613ede45a099fc3946673f390c
Source dataset
uspto-grants-2010_02
Patent number
US07659294B2

Reaction notes

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