8-Hydroxyquinoline → HCID 19597399, compound

HRID 611529Notes

Reaction equation

HRID 611529 reaction equation
[NH2:1][C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][C:14](I)=[CH:13][CH:12]=3)=[CH:9][N:8]([C:18]([CH3:21])([CH3:20])[CH3:19])[C:4]=2[N:5]=[CH:6][N:7]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:28][N:29]([C:33]1[CH:38]=[CH:37][C:36]([OH:39])=[CH:35][CH:34]=1)[C:30](=[O:32])[CH3:31].OC1C=CC=C2C=1N=CC=C2>[Cu]Cl.CC(N(C)C)=O>[NH2:1][C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([O:39][C:36]4[CH:35]=[CH:34][C:33]([N:29]([CH3:28])[C:30](=[O:32])[CH3:31])=[CH:38][CH:37]=4)=[CH:13][CH:12]=3)=[CH:9][N:8]([C:18]([CH3:21])([CH3:20])[CH3:19])[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

7

Reactant 4

HCID 19238-HydroxyquinolineHCID 11430Potassium CarbonateHCID 221111N-METHYL P-HYDROXYACETANILIDEHCID 19597408HCID 19597408, compound

Product 1

HCID 19597399HCID 19597399, compound

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 31374DimethylacetamideSolvent

Procedure

In a similar manner to Example 9, a mixture of 4-amino-5-(4-iodophenyl)-7-(tert-butyl)pyrrolo[2,3-d]pyrimidine (100 mg), potassium carbonate (104 mg), N-methyl-(4-acetamido)phenol (120 mg), 8-hydroxyquinoline (8 mg), copper (I) chloride (5 mg) and dimethylacetamide (8 ml) gave N-{4-[4-(4-amino-7-tert-butylpyrrolo[2,3-d]-pyrimidin-5-yl)phenoxy]phenyl}-N-methylacetamide. This structure was confirmed by 1H nmr.

Sources & evidence

ORD record
ord-3dc0139738654c8fae8e5ee59ef87680
Source dataset
uspto-grants-1999_12
Patent number
US06001839

Reaction notes

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