Cesium carbonate → HCID 58446983, compound

HRID 1045729Notes

Reaction equation

HRID 1045729 reaction equation
Br[C:2]1[N:3]=[C:4]([N:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]2)[C:5]2[N:6]([CH:8]=[N:9][N:10]=2)[CH:7]=1.[S:24]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25]1.C([O-])([O-])=O.[Cs+].[Cs+].O1CCOCC1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[S:24]1[CH:28]=[CH:27][C:26]([C:2]2[N:3]=[C:4]([N:11]3[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]3)[C:5]3[N:6]([CH:8]=[N:9][N:10]=3)[CH:7]=2)=[CH:25]1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 312751,4-DioxaneHCID 581760Thiophene-3-boronic acidHCID 58447041HCID 58447041, compound

Product 1

HCID 58446983HCID 58446983, compoundYield 99.5%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Procedure

A 100 mL round bottom flask was charged with tert-butyl 4-(6-bromo-[1,2,4]triazolo[4,3-a]pyrazin-8-yl)piperazine-1-carboxylate (1.0 g, 2.6 mmol), thiophen-3-ylboronic acid (0.50 g, 3.9 mmol), Pd(PPh3)4 (0.30 g, 0.26 mmol), Cs2CO3 (1.27 g, 3.9 mmol), 1,4-dioxane (25 mL) and water (25 mL). The resulting mixture was refluxed under N2 overnight. Reaction progress was monitored by TLC (EtOAc/petroleum ether=1:2). Work-up: the reaction mixture was extracted with EtOAc (50 mL). The organic solution was washed with brine (40 mL), dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was further purified by flash column chromatography on silica gel with 10% EtOAc in petroleum ether, to afford 1.0 g (99%) of the product as a yellow solid.

Workup

  1. temperatureThe resulting mixture was refluxed under N2 overnight
  2. customReaction progress
  3. extractionthe reaction mixture was extracted with EtOAc (50 mL)
  4. washThe organic solution was washed with brine (40 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was further purified by flash column chromatography on silica gel with 10% EtOAc in petroleum ether

Sources & evidence

ORD record
ord-a29df5a0eb884f37a31cb889c6d84382
Source dataset
uspto-grants-2013_10
Patent number
US08569300B2

Reaction notes

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