1-Methyl-1H-1,2,3-triazole → 3-chloro-6-(1-methyl-1H-1,2,3-triazol-5-yl)isoquinoline

HRID 523055Notes

Reaction equation

HRID 523055 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[N:7][C:6]([Cl:12])=[CH:5]2.[CH3:13][N:14]1[CH:18]=[CH:17][N:16]=[N:15]1.CC([O-])=O.[K+]>CC(N(C)C)=O.[Cl-].[Na+].O.CC([O-])=O.CC([O-])=O.[Pd+2]>[Cl:12][C:6]1[N:7]=[CH:8][C:9]2[C:4]([CH:5]=1)=[CH:3][C:2]([C:18]1[N:14]([CH3:13])[N:15]=[N:16][CH:17]=1)=[CH:11][CH:10]=2

Participants

7

Reactant 3

HCID 1401191-Methyl-1H-1,2,3-triazoleHCID 517044Potassium AcetateHCID 226075306-Bromo-3-chloroisoquinoline

Product 1

HCID 899955733-chloro-6-(1-methyl-1H-1,2,3-triazol-5-yl)isoquinolineYield 31.1%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 31374DimethylacetamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A suspension of 6-bromo-3-chloroisoquinoline (60 mg, 0.25 mmol), 1-methyl-1H-1,2,3-triazole (41 mg, 0.50 mmol), Pd(OAc)2 (2.22 mg, 9.9 umol) and KOAc (49 mg, 0.50 mmol) in DMA (4 mL) was stirred at 1500 under microwave irradiation for 60 minutes. The reaction mixture was diluted with brine and extracted with EtOAc. The combined organic layers were washed with water and dried with Na2SO4 and concentrated in vacuo. The residue was purified using Biotage silica gel column chromatography eluting with 40% EtOAc in cyclohexane to afford the title compound as a white solid (19 mg, 31%).

Workup

  1. extractionextracted with EtOAc
  2. washThe combined organic layers were washed with water
  3. dry with materialdried with Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified
  6. washeluting with 40% EtOAc in cyclohexane

Sources & evidence

ORD record
ord-16cd4f16f240487fbcf5049959197323
Source dataset
uspto-grants-2016_05
Patent number
US09334286B2

Reaction notes

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