8-Hydroxyquinoline → HCID 56941125, compound

HRID 1843994Notes

Reaction equation

HRID 1843994 reaction equation
[C:1]1(=[O:14])[C:13]2[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[NH:6][C:5]=2[CH:4]=[CH:3][NH:2]1.I[C:16]1[CH:17]=[N:18][CH:19]=[CH:20][C:21]=1[CH3:22].OC1C=CC=C2C=1N=CC=C2.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl.[Cu]I.CO.CS(C)=O>[CH3:22][C:21]1[CH:20]=[CH:19][N:18]=[CH:17][C:16]=1[N:2]1[CH:3]=[CH:4][C:5]2[NH:6][C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=3[C:13]=2[C:1]1=[O:14]

Participants

9

Reactant 4

HCID 19238-HydroxyquinolineHCID 11430Potassium CarbonateHCID 121012772,5-dihydro-1H-pyrido[4,3-b]indol-1-oneHCID 144235133-Iodo-4-methylpyridine

Product 1

HCID 56941125HCID 56941125, compoundYield 5.4%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
150 °C

Procedure

2,5-dihydro-1H-pyrido[4,3-b]indol-1-one (I-62a: 500 mg, 2.71 mmol), 3-iodo-4-methylpyridine (892 mg, 4 mmol), 8-hydroxy quinoline (79 mg, 0.542 mmol) and K2CO3 (560 mg, 4.06 mmol) were added to a previously degassed solution of DMSO (10 mL). This was followed by the addition of CuI (103.2 mg, 0.542 mmol) and the resulting reaction mass was heated at 150° C. for 16 hours in a sealed tube. The reaction was monitored by TLC (5% methanol in DCM). The reaction mass was quenched with water, diluted using ethyl acetate and filtered. The filtrate was extracted using ethyl acetate, washed the organic layer with water, brine solution, dried over Na2SO4 and concentrated under reduced pressure to afford the crude product. Purification by column chromatography on silica gel (1% methanol in DCM), followed by preparative HPLC afforded 40 mg of the product (5.4% yield).

Workup

  1. customthe resulting reaction mass
  2. customThe reaction mass was quenched with water
  3. additiondiluted
  4. filtrationfiltered
  5. extractionThe filtrate was extracted
  6. washwashed the organic layer with water, brine solution
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated under reduced pressure
  9. customto afford the crude product
  10. customPurification by column chromatography on silica gel (1% methanol in DCM)

Sources & evidence

ORD record
ord-a48d2795cbd54e9a82aea4a5283e85f0
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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