Triethylamine → HCID 68586542, compound

HRID 17532Notes

Reaction equation

HRID 17532 reaction equation
F[C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:6][C:5]([C:14]#[N:15])=[C:4]([N+:16]([O-:18])=[O:17])[CH:3]=1.C(N(CC)CC)C.[CH3:26][N:27]([CH3:33])[C@H:28]1[CH2:32][CH2:31][NH:30][CH2:29]1.C(=O)([O-])O.[Na+]>CS(C)=O.C(OCC)(=O)C>[CH3:26][N:27]([CH3:33])[C@H:28]1[CH2:32][CH2:31][N:30]([C:2]2[C:7]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)=[CH:6][C:5]([C:14]#[N:15])=[C:4]([N+:16]([O-:18])=[O:17])[CH:3]=2)[CH2:29]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 7019156(3S)-(-)-3-(Dimethylamino)pyrrolidineHCID 685844646-Fluoro-4-nitrobiphenyl-3-carbonitrile

Product 1

HCID 68586542HCID 68586542, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

6-Fluoro-4-nitrobiphenyl-3-carbonitrile (I-241) (6.0 g, 24.77 mmol) was dissolved in dimethyl sulfoxide (60 ml), and at room temperature, triethylamine (6.9 ml, 49.54 mmol) and (3S)-3-(dimethylamino)pyrrolidine (3.77 ml, 29.73 mmol) were added. After stirring at the same temperature for 19 hours, the reaction liquid was fractionated with ethyl acetate and an aqueous saturated sodium hydrogencarbonate solution. The organic layer was washed with saturated brine, then dried over anhydrous sodium sulfate. The insoluble matter was separated by filtration, the solvent was evaporated away, and the resulting residue was subjected to column chromatography with silica gel, and the fraction with chloroform:methanol=95:5 gave the entitled compound (7.90 g, 95%) as an orange powder.

Workup

  1. customthe reaction liquid
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe insoluble matter was separated by filtration
  5. customthe solvent was evaporated away

Sources & evidence

ORD record
ord-764b17c20c894293869a10be8ba90ac2
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

Loading…