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

HRID 1919673Notes

Reaction equation

HRID 1919673 reaction equation
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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

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

Procedure

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]+.

Workup

  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

Sources & evidence

ORD record
ord-bb101d80efe34071a394b2d19a9673fe
Source dataset
uspto-grants-2012_05
Patent number
US08168651B2

Reaction notes

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