Cesium carbonate → HCID 53662609, compound

HRID 1198505Notes

Reaction equation

HRID 1198505 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]3[NH:14][C:13]4[CH2:15][CH2:16][NH:17][CH2:18][C:12]=4[C:7]=3[CH:8]=[N:9]2)=[CH:4][CH:3]=1.F[C:20]1[CH:30]=[CH:29][C:23]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:22][CH:21]=1.C[N+]1([O-])CCOCC1.C([O-])([O-])=O.[Cs+].[Cs+]>O.CS(C)=O>[CH2:27]([O:26][C:24](=[O:25])[C:23]1[CH:29]=[CH:30][C:20]([N:17]2[CH2:16][CH2:15][C:13]3[NH:14][C:6]4[C:5]5[C:10](=[CH:11][C:2]([Cl:1])=[CH:3][CH:4]=5)[N:9]=[CH:8][C:7]=4[C:12]=3[CH2:18]2)=[CH:21][CH:22]=1)[CH3:28]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 67976Benzoic acid, 4-fluoro-, ethyl esterHCID 82029Methyl morpholine oxideHCID 14069786HCID 14069786, compound

Product 1

HCID 53662609HCID 53662609, compoundYield 2.3%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 1.5 g (5.8 mmol) of 3-chloro-8,9,10,11-tetrahydro-7H-pyrido[3',4':4,5]pyrrolo[3,2-c]quinoline, 0.979 g (5.8 mmol) of ethyl 4-fluorobenzoate, 0.68 g (5.8 mmol) of 4-methylmorpholine N-oxide, 3.78 g (11.6 mmol) of Cs2CO3 and 10 ml of dimethylsulfoxide is stirred overnight at 80° C. The reaction mixture is allowed to cool and is diluted with water to yield a brown precipitate which is collected by filtration and dried. The crude product is purified by flash column chromatography (5% methanol in chloroform) to yield 0.055 g (2%) of the title compound as a yellow solid: m.p. 241°-243° C.; m/e 405.

Workup

  1. temperatureto cool
  2. customto yield a brown precipitate which
  3. filtrationis collected by filtration
  4. customdried
  5. customThe crude product is purified by flash column chromatography (5% methanol in chloroform)

Sources & evidence

ORD record
ord-4b4eef85c13746ab9225876d73048741
Source dataset
uspto-grants-1994_01
Patent number
US05281608

Reaction notes

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