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8-Hydroxyquinoline → HCID 56942895, compound

HRID 1843915
Notes
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Reaction equation

HRID 1843915 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][NH:9][C:10]2=[O:13])=[CH:5][CH:4]=1.Br[C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1.OC1C=CC=C2C=1N=CC=C2.C(=O)([O-])[O-].[K+].[K+]>[Cu](I)I.CS(C)=O>[N:19]1[CH:20]=[CH:21][CH:22]=[C:17]([N:9]2[CH:8]=[CH:7][C:6]3[C:11](=[CH:12][C:3]([C:2]([F:1])([F:14])[F:15])=[CH:4][CH:5]=3)[C:10]2=[O:13])[CH:18]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 19238-HydroxyquinolineHCID 11430Potassium CarbonateHCID 122863-BromopyridineHCID 426091807-(trifluoromethyl)isoquinolin-1(2H)-one

Product 1

HCID 56942895HCID 56942895, compoundYield 70.58%

Reagents, catalysts & solvents 2

HCID 83717
Copper iodide
Catalyst
HCID 679Dimethyl SulfoxideSolvent

Procedure

Using analogous reaction conditions as described in Example 1, 7-trifluoromethyl-2H-isoquinolin-1-one (I-29d: 0.12 g, 0.56 mmol) was reacted with 3-bromo-pyridine (0.106 g, 0.6 mmol), DMSO (2 mL), copper iodide (0.021 g, 0.12 mmol), 8-hydroxy-quinoline (0.018 g, 0.12 mmol) and potassium carbonate (0.15 g, 1.1 mmol) to afford the crude product. Purification by column chromatography on silica gel (0.5% methanol in DCM) afforded 96 mg of the product (70.58% yield).

Workup

  1. customreaction conditions
  2. customto afford the crude product
  3. customPurification by column chromatography on silica gel (0.5% methanol in DCM)

Sources & evidence

ORD record
ord-a045caccf291471fadef1c57d49dede4
Source dataset
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08946260B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes