8-Hydroxyquinoline → HCID 66807170, compound

HRID 1843995Notes

Reaction equation

HRID 1843995 reaction equation
CC1C=CN=CC=1N1C=CC2NC3C=CC=CC=3C=2C1=O.[C:22]1(=[O:35])[C:34]2[C:33]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[NH:27][C:26]=2[CH:25]=[CH:24][NH:23]1.Br[C:37]1[CH:38]=[N:39][CH:40]=[CH:41][C:42]=1[C:43]([F:46])([F:45])[F:44].OC1C=CC=C2C=1N=CC=C2.C([O-])([O-])=O.[K+].[K+]>[Cu](I)I.CS(C)=O>[F:44][C:43]([F:46])([F:45])[C:42]1[CH:41]=[CH:40][N:39]=[CH:38][C:37]=1[N:23]1[CH:24]=[CH:25][C:26]2[NH:27][C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][C:33]=3[C:34]=2[C:22]1=[O:35]

Participants

8

Reactant 5

HCID 19238-HydroxyquinolineHCID 11430Potassium CarbonateHCID 121012772,5-dihydro-1H-pyrido[4,3-b]indol-1-oneHCID 199372633-Bromo-4-(trifluoromethyl)pyridineHCID 56941125HCID 56941125, compound

Product 1

HCID 66807170HCID 66807170, compoundYield 1.5%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

Using analogous reaction conditions and work up as described for the preparation of 62A above, 2,5-dihydro-1H-pyrido[4,3-b]indol-1-one (I-62a: 200 mg, 1.08 mmol) was reacted with 3-bromo-4-trifluoromethylpyridine (368.4 mg, 1.63 mmol), 8-hydroxy quinoline (31.3 mg, 0.216 mmol), K2CO3 (223.5 mg, 1.62 mmol), copper iodide (41.14 mg, 0.216 mmol) and DMSO (5 mL) to afford the crude product. Purification by column chromatography on silica gel (2% methanol in DCM), followed by preparative HPLC afforded 5 mg of the product (1.5% yield).

Workup

  1. customreaction conditions
  2. customto afford the crude product
  3. customPurification by column chromatography on silica gel (2% methanol in DCM)

Sources & evidence

ORD record
ord-7adf1c703b604a279a221433260b2f0a
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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