Potassium Carbonate → HCID 66745361, compound

HRID 1959388Notes

Reaction equation

HRID 1959388 reaction equation
[C:1]([O:5][C:6]([N:8]([C:16]1[C:21]([C:22]2[N:30]=[C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][N:24]3[N:23]=2)=[N:20][C:19](Br)=[CH:18][N:17]=1)[C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].CC1(C)C(C)(C)OB([C:40]2[CH2:41][CH2:42][N:43]([C:46]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:47])[CH2:44][CH:45]=2)O1.C([O-])([O-])=O.[K+].[K+].CCOC(C)=O.O>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[N:30]1[C:22]([C:21]2[N:20]=[C:19]([C:40]3[CH2:45][CH2:44][N:43]([C:46]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:47])[CH2:42][CH:41]=3)[CH:18]=[N:17][C:16]=2[N:8]([C:9]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:15])[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[N:23][N:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=12

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 4642098Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylateHCID 22728543Water ethylacetateHCID 86662076HCID 86662076, compound

Product 1

HCID 66745361HCID 66745361, compoundYield 69.3%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Tert-butyl N-tert-butoxycarbonyl-3-([1,2,4]triazolo[1,5-a]pyridin-2-yl)-5-bromopyrazin-2-ylcarbamate (92 mg, 0.1872 mmol) was dissolved in DMF (1.5 mL) and treated with tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylate (86.83 mg, 0.2808 mmol), PdCl2(PPh3)2 (13.14 mg, 0.01872 mmol) and K2CO3 (280.8 μL of 2 M, 0.5616 mmol). The mixture was allowed to heat at 100° C. for 1 hour and then allowed to cool to ambient temperature. The reaction was treated with EtOAc/water, the organics separated, washed with water (2×) followed by brine (2×), dried (MgSO4), filtered and concentrated to a brown oil. The residue was purified by column chromatography (ISCO Companion™, 12 g column, 0-100% EtOAc/Petrol) to afford the title compound as a white solid (77 mg, 69% Yield). MS (ES+) 594.0

Workup

  1. temperatureto cool to ambient temperature
  2. washthe organics separated, washed with water (2×)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated to a brown oil
  6. customThe residue was purified by column chromatography (ISCO Companion™, 12 g column, 0-100% EtOAc/Petrol)

Sources & evidence

ORD record
ord-91b1909c8b76474f9795bd172540d396
Source dataset
uspto-grants-2013_04
Patent number
US08410112B2

Reaction notes

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