Potassium Carbonate → HCID 135979606, compound

HRID 1784017Notes

Reaction equation

HRID 1784017 reaction equation
[CH2:1]([O:3][C:4](=[O:29])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N:11]([C:19]2[C:20]3[N:21]([N:26]=[CH:27][N:28]=3)[C:22](Br)=[CH:23][N:24]=2)[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH:6]=1)[CH3:2].CC1(C)C(C)(C)OB([C:38]2[CH:39]=[N:40][NH:41][CH:42]=2)O1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O>[CH2:1]([O:3][C:4](=[O:29])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N:11]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C:19]2[C:20]3[N:21]([N:26]=[CH:27][N:28]=3)[C:22]([C:38]3[CH:39]=[N:40][NH:41][CH:42]=3)=[CH:23][N:24]=2)[CH:6]=1)[CH3:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 57590006HCID 57590006, compound

Product 1

HCID 135979606HCID 135979606, compoundYield 108.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
115 °C

Procedure

Nitrogen is bubbled through a mixture of 3-[(5-bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-yl)-tert-butoxycarbonyl-amino]benzoic acid ethyl ester (0.58 g, 1.25 mmol), 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (0.49 g, 2.50 mmol), K2CO3 (0.35 g, 2.50 mmol) and Pd(dppf)Cl2DCM (102 mg, 0.125 mmol) in dioxane (37.5 mL) and water (9.6 mL). A condenser is fitted to the flask, the system is evacuated and purged with N2 (g) and then heated at 115° C. for 25 min. The heating bath is removed and CO2 (s) is added to cool and buffer the system. The solvent is removed under reduced pressure and the residue is purified by silica chromatography, eluting with 10% to 50% ethyl acetate in DCM, to afford the title compound as an orange oil (0.61 g, >100%) which is used without further purification.

Workup

  1. customA condenser is fitted to the flask
  2. customthe system is evacuated
  3. custompurged with N2 (g)
  4. customThe heating bath is removed
  5. additionCO2 (s) is added
  6. temperatureto cool
  7. customThe solvent is removed under reduced pressure
  8. customthe residue is purified by silica chromatography
  9. washeluting with 10% to 50% ethyl acetate in DCM

Sources & evidence

ORD record
ord-330b23e505d84149a2cbb0351f283546
Source dataset
uspto-grants-2009_03
Patent number
US07501411B2

Reaction notes

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