Cesium carbonate → HCID 58447049, compound

HRID 1045775Notes

Reaction equation

HRID 1045775 reaction equation
Br[C:2]1[C:3]2[N:4]([N:21]=[CH:22][N:23]=2)[C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)=[N:6][CH:7]=1.[S:24]1[CH:28]=[CH:27][CH:26]=[C:25]1B(O)O.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][CH:26]=[C:25]1[C:2]1[C:3]2[N:4]([N:21]=[CH:22][N:23]=2)[C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 312751,4-DioxaneHCID 27339602-Thiopheneboronic acidHCID 58447029HCID 58447029, compound

Product 1

HCID 58447049HCID 58447049, compoundYield 82.4%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A 50 mL round bottom flask was charged with tert-butyl 4-(8-bromo-[1,2,4]triazolo[1,5-c]pyrimidin-5-yl)piperazine-1-carboxylate (0.6 g, 1.57 mmol), thiophene-2-boronic acid (0.35 g, 2.74 mmol), tetrakis(triphenylphosphine)palladium(0) (0.25 g, 0.21 mmol), Cs2CO3 (2 g, 6.36 mmol), 1,4-dioxane (20 mL) and water (5 mL). After the air was purged by bubbling N2 into the solution, the resulting mixture was stirred at 100° C. under N2 overnight. Work-up: the reaction mixture was diluted with water and extracted with CH2Cl2 (50 mL×3). The combined organic layers were dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel to afford 0.5 g (82%) of the product as a white solid.

Workup

  1. customAfter the air was purged
  2. customby bubbling N2 into the solution
  3. additionthe reaction mixture was diluted with water
  4. extractionextracted with CH2Cl2 (50 mL×3)
  5. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-110aa482cee447e5bfce32b802410b7d
Source dataset
uspto-grants-2013_10
Patent number
US08569300B2

Reaction notes

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