8-Hydroxyquinoline → HCID 90409343, compound

HRID 2177570Notes

Reaction equation

HRID 2177570 reaction equation
[NH:1]1[C:9]2[CH2:8][CH2:7][N:6]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH:5]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:4]=2[N:3]=[CH:2]1.I[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.OC1C=CC=C2C=1N=CC=C2.C([O-])([O-])=O.[Cs+].[Cs+]>CS(C)=O.O.[Cu-]=O>[C:23]1([N:1]2[C:9]3[CH2:8][CH2:7][N:6]([C:10]([O:12][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:11])[CH:5]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:4]=3[N:3]=[CH:2]2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

8

Reactant 4

HCID 19238-HydroxyquinolineHCID 10796Cesium carbonateHCID 11575IodobenzeneHCID 90409708HCID 90409708, compound

Product 1

HCID 90409343HCID 90409343, compoundYield 50.2%

Reagents, catalysts & solvents 3

HCID 178419072HCID 178419072, compoundCatalystHCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A solution of 5-tert-butyl 4-ethyl 6,7-dihydro-1H-imidazo[4,5-c]pyridine-4,5(4H)-dicarboxylate (0.65 g, 2.20 mmol), iodobenzene (0.45 g, 2.20 mmol), copper (I) oxide (0.03 g, 0.22 mmol), 8-hydroxyquinoline (0.06 g, 0.44 mmol), and Cs2CO3 (1.40 g, 4.40 mmol) in DMSO (2 mL) was irradiated in a microwave apparatus for 1 hour at 140° C. The reaction was diluted with H2O (100 mL) and extracted with EtOAc (75 mL×3). The organic layers were combined, dried (Na2SO4), and concentrated. Chromatography of the resulting residue (SiO2; MeOH(NH3):DCM) gave the title compound (0.41 g, 50%). MS (ESI): mass calculated for C20H25N3O4, 371.2. m/z found 272.2 [M+H—BOC]+.

Workup

  1. extractionextracted with EtOAc (75 mL×3)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-3b9a60627c774fcf8dd79ef2f57093a5
Source dataset
uspto-grants-2015_06
Patent number
US09066946B2

Reaction notes

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