Water → 4-Oxo-4,5-dihydrothieno[2,3-c]quinoline-7-carbonitrile

HRID 1919673노트

반응식

HRID 1919673 반응식
CO[C:3]([C:5]1[S:6][CH:7]=[CH:8][C:9]=1Br)=[O:4].Cl.[NH2:12][C:13]1[CH:18]=[C:17]([C:19]#[N:20])[CH:16]=[CH:15][C:14]=1B(O)O.C(=O)([O-])[O-].[Cs+].[Cs+].O>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[O:4]=[C:3]1[C:5]2[S:6][CH:7]=[CH:8][C:9]=2[C:14]2[CH:15]=[CH:16][C:17]([C:19]#[N:20])=[CH:18][C:13]=2[NH:12]1

참가 물질

7

반응물 4

HCID 962WaterHCID 10796Cesium carbonateHCID 2740074Methyl 3-bromothiophene-2-carboxylateHCID 441187662-Amino-4-cyanobenzeneboronic acid hydrochloride

생성물 1

HCID 575006864-Oxo-4,5-dihydrothieno[2,3-c]quinoline-7-carbonitrile

시약·촉매·용매 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 312751,4-Dioxane용매

실험 절차

Methyl-3-bromothiophene carboxylate (1.0 eq, 2.42 g, 10.95 mmol), 2-amino-4-cyanophenylboronic acid hydrochloride (1.05 eq, 2.28 g, 11.49 mmol) and cesium carbonate (2.0 eq, 7.13 g, 21.9 mmol) were suspended in dioxane (25 ml) containing 5% water. The mixture was degassed by bubbling nitrogen for 10 minutes. PdCl2(dppf) (0.05 eq, 400 mg, 0.55 mmol) was added and the mixture was stirred at reflux for 1.5 hours. The mixture was cooled down, the solid filtered, washed with dioxane, water and methanol. After drying in vacuo, 4-oxo-4,5-dihydrothieno[2,3-c]quinoline-7-carbonitrile was isolated as a solid (1.81 g, 73% yield). LCMS (ES) m/z 227 [M+1]+.

후처리

  1. customThe mixture was degassed
  2. customby bubbling nitrogen for 10 minutes
  3. temperatureat reflux for 1.5 hours
  4. temperatureThe mixture was cooled down
  5. filtrationthe solid filtered
  6. washwashed with dioxane, water and methanol
  7. customAfter drying in vacuo

출처 및 근거

ORD 기록
ord-bb101d80efe34071a394b2d19a9673fe
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08168651B2

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