Dimethyl Sulfoxide → HCID 19760327, compound

HRID 1586968Notes

Reaction equation

HRID 1586968 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:27]=[CH:26][C:23]([C:24]#[N:25])=[CH:22][CH:21]=1.C([O-])([O-])=[O:29].[K+].[K+].CS(C)=O>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[NH:14][C:13]([CH2:15][CH2:16][NH:17][C:20]4[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[CH:22][CH:21]=4)=[C:12]([CH:18]=[O:29])[C:7]=3[CH:8]=[N:9][C:10]=2[CH:11]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 145174-FluorobenzonitrileHCID 14069786HCID 14069786, compound

Product 1

HCID 19760327HCID 19760327, compoundYield 4.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 1.00 g (3.88 mmol) of 3-chloro-8,9,10,11-tetrahydro-7H-pyrido[3',4':4,5]pyrrolo[3,2-c]quinoline prepared according to the method reported in J. Heterocyclic Chemistry, 25, 535 (1988), 0.47 g (3.88 mmol) of p-fluorobenzonitrile, 0.54 g (3.88 mmol) of K2CO3 and 8 ml of dimethyl sulfoxide is stirred at 80° C. for 3 days. The reaction mixture is allowed to cool and is diluted with water producing 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 0.06 g (4%) of the title compound as a yellow solid: m.p. 203°-206° C.; IR (KBr) 3380, 3200, 2200, 1650, 1600 cm-1 ; NMR (DMSO-d6) δ13.1 (s, 1H), 10.1 (s, 1H), 9.5 (s, 1H), 8.4 (d, 1H), 8.1 (d, 1H), 7.8-7.7 (m, 1H), 7.4 (d, 2H), 6.9 (t, 1H), 6.7 (d, 2H), 3.6 (q, 2H), 3.4 (t, 2H); m/e 375 (M+H).

Workup

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

Sources & evidence

ORD record
ord-a5bc2084573f4f3d99597be21f0ad92d
Source dataset
uspto-grants-1993_06
Patent number
US05216162

Reaction notes

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