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

HRID 1817823노트

반응식

HRID 1817823 반응식
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

참가 물질

8

반응물 4

HCID 11430Potassium CarbonateHCID 2776315(5-Phenylthiophen-2-yl)boronic acidHCID 21226206Ethyl acetate hexaneHCID 247779422-Chloro-5-oxo-5,6,7,8-tetrahydroquinoline-3-carbonitrile2회

생성물 1

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

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 312751,4-Dioxane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f9bf2a320ee44ca581c1f20e596b1a9e
출처 데이터셋
uspto-grants-2009_10
특허 번호
US07598384B2

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