1,2-Dimethylimidazole → HCID 89995597, compound

HRID 523098Notes

Reaction equation

HRID 523098 reaction equation
Br[C:2]1[N:7]=[C:6]([O:8][CH3:9])[C:5]([NH2:10])=[CH:4][CH:3]=1.[CH3:11][N:12]1[CH:16]=[CH:15][N:14]=[C:13]1[CH3:17].CC([O-])=O.[K+]>CC(N(C)C)=O.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:11][N:12]1[C:16]([C:2]2[N:7]=[C:6]([O:8][CH3:9])[C:5]([NH2:10])=[CH:4][CH:3]=2)=[CH:15][N:14]=[C:13]1[CH3:17]

Participants

6

Reactant 3

HCID 156171,2-DimethylimidazoleHCID 517044Potassium AcetateHCID 105361376-Bromo-2-methoxypyridin-3-amine

Product 1

HCID 89995597HCID 89995597, compoundYield 16.5%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 31374DimethylacetamideSolvent

Procedure

A suspension of 6-bromo-2-methoxypyridin-3-amine (96 mg, 0.473 mmol), 1,2-dimethyl-1H-imidazole (91 mg, 0.946 mmol), Pd(OAc)2 (4.3 mg, 0.019 mmol), KOAc (93 mg, 0.95 mmol) in DMA (3 mL) was stirred at 1500 under microwave irradiation for 8 hours. The reaction mixture was filtered, diluted with NaCl solution and extracted with EtOAc. The organic layer was purified by eluting through an SCX-2 column using 2M NH3/MeOH followed by Biotage silica gel column chromatography eluting with 0-4% MeOH/EtOAc to give the title compound as pink solid (17 mg, 16%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. additiondiluted with NaCl solution
  3. extractionextracted with EtOAc
  4. customThe organic layer was purified
  5. washby eluting through an SCX-2 column
  6. washeluting with 0-4% MeOH/EtOAc

Sources & evidence

ORD record
ord-7663a71618584c9f9ac14ad722f6976f
Source dataset
uspto-grants-2016_05
Patent number
US09334286B2

Reaction notes

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