8-Hydroxyquinoline → HCID 90408578, compound

HRID 2177566Notes

Reaction equation

HRID 2177566 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.Br[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=1.OC1C=CC=C2C=1N=CC=C2.C([O-])([O-])=O.[Cs+].[Cs+]>CS(C)=O.O.[Cu-]=O>[N:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[N:1]1[C:9]2[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]=2[N:3]=[CH:2]1

Participants

8

Reactant 4

HCID 19238-HydroxyquinolineHCID 79732-BromopyridineHCID 10796Cesium carbonateHCID 90409708HCID 90409708, compound

Product 1

HCID 90408578HCID 90408578, compoundYield 40%

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 (0.50 g, 1.69 mmol), 2-bromo-pyridine (0.27 g, 1.69 mmol), copper (I) oxide (0.03 g, 0.17 mmol), 8-hydroxyquinoline (0.05 g, 0.34 mmol), and Cs2CO3 (1.10 g, 3.39 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 (0.25 g, 40%). MS (ESI): mass calculated for C19H24N4O4, 372.2. m/z found 273.2 [M+H—BOC]+.

Workup

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

Sources & evidence

ORD record
ord-8f8f10380b424999b8e2fa6a34f9cb13
Source dataset
uspto-grants-2015_06
Patent number
US09066946B2

Reaction notes

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