Dimethylformamide → HCID 11573946, compound

HRID 2267169Notes

Reaction equation

HRID 2267169 reaction equation
I[C:2]1[N:3]=[N:4][N:5]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:6]=1[CH2:7][CH2:8][CH3:9].[C:16](=[O:19])([O-])[O-:17].[K+].[K+].[CH3:22][N:23]([CH3:26])C=O>>[C:10]1([N:5]2[C:6]([CH2:7][CH2:8][CH3:9])=[C:2]([C:6]3[CH2:7][CH:22]([C:16]([O:17][CH:10]([CH3:15])[CH3:11])=[O:19])[NH:23][CH2:26][CH:2]=3)[N:3]=[N:4]2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 68429651HCID 68429651, compound

Product 1

HCID 11573946HCID 11573946, compound

Conditions

Temperature
80 °C

Procedure

In a nitrogen atmosphere, 30 mg of 4-iodo-1-phenyl-5-propyl-1H-[1,2,3]-triazole prepared in the above 2), 34 mg of isopropyl 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaboran-2-yl)-1,2,3,6-tetrahydropyridine-carboxylate prepared in Example 45-6 and 26 mg of potassium carbonate were dissolved in 3 ml of N,N-dimethylformamide, 7.7 mg of [1,1-bis(diphenylphosphino)-ferrocene]dichloropalladium was added thereto and the mixture was stirred with heating at 80° C. for one night. After the reaction solution was cooled down to room temperature, insoluble matters were removed by filtering through Celite. Water was added to the filtrate, the mixture was extracted with diethyl ether and the diethyl ether layer washed with a saturated saline solution and dried over sodium sulfate. After the solvent was evaporated in vacuo, the residue was separated and purified by a thin-layer chromatography (hexane/ethyl acetate=2/1) to give 9.04 mg of a white solid.

Workup

  1. temperatureAfter the reaction solution was cooled down to room temperature
  2. custominsoluble matters were removed
  3. filtrationby filtering through Celite
  4. additionWater was added to the filtrate
  5. extractionthe mixture was extracted with diethyl ether
  6. washthe diethyl ether layer washed with a saturated saline solution
  7. dry with materialdried over sodium sulfate
  8. customAfter the solvent was evaporated in vacuo
  9. customthe residue was separated
  10. custompurified by a thin-layer chromatography (hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-698d93672b51443ca84ee21bacec29e5
Source dataset
uspto-grants-2010_12
Patent number
US07858800B2

Reaction notes

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