Potassium Carbonate → 5-Oxo-2-(5-phenyl-thiophen-2-yl)-5,6,7,8-tetrahydro-quinoline-3-carbonitrile

HRID 1817823Notes

Reaction equation

HRID 1817823 reaction equation
Cl[C:2]1[C:11]([C:12]#[N:13])=[CH:10][C:9]2[C:8](=[O:14])[CH2:7][CH2:6][CH2:5][C:4]=2[N:3]=1.[C:15]1([C:21]2[S:25][C:24](B(O)O)=[CH:23][CH:22]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C([O-])([O-])=O.[K+].[K+].CCCCCC.CCOC(C)=O>O1CCOCC1.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.O>[O:14]=[C:8]1[CH2:7][CH2:6][CH2:5][C:4]2[N:3]=[C:2]([C:24]3[S:25][C:21]([C:15]4[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=4)=[CH:22][CH:23]=3)[C:11]([C:12]#[N:13])=[CH:10][C:9]1=2

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 2776315(5-Phenylthiophen-2-yl)boronic acidHCID 21226206Ethyl acetate hexaneHCID 247779422-Chloro-5-oxo-5,6,7,8-tetrahydroquinoline-3-carbonitrile2×

Product 1

HCID 114162475-Oxo-2-(5-phenyl-thiophen-2-yl)-5,6,7,8-tetrahydro-quinoline-3-carbonitrileYield 46%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-chloro-5-oxo-5,6,7,8-tetrahydro-quinoline-3-carbonitrile (300 mg, 1.46 mmol) and 5-phenyl-thiophen-2-yl-boronic acid (446 mg, 2.19 mmol) in dioxane (3 ml) under an argon atmosphere was added tetrakis(triphenylphosphine)palladium (85 mg, 0.073 mmol) and 2M aqueous K2CO3 (0.7 ml). The mixture was stirred at reflux till complete (TLC; hexane-EtOAc, 2:1) consumption of 2-chloro-5-oxo-5,6,7,8-tetrahydro-quinoline-3-carbonitrile. Then water was added and the mixture was extracted by dichloromethane. The extract was concentrated under reduced pressure and the residue was purified by column chromatography on silica gel (CH2Cl2-Hexane, 1:1), then heated under reflux in ethyl alcohol and filtered to give the title compound (220 mg, 46%) as a dark yellow solid.

Workup

  1. extractionthe mixture was extracted by dichloromethane
  2. concentrationThe extract was concentrated under reduced pressure
  3. customthe residue was purified by column chromatography on silica gel (CH2Cl2-Hexane, 1:1)
  4. temperatureheated
  5. temperatureunder reflux in ethyl alcohol
  6. filtrationfiltered

Sources & evidence

ORD record
ord-f9bf2a320ee44ca581c1f20e596b1a9e
Source dataset
uspto-grants-2009_10
Patent number
US07598384B2

Reaction notes

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