Sodium Carbonate → HCID 68295200, compound

HRID 1909170Notes

Reaction equation

HRID 1909170 reaction equation
[CH:1]([N:4]1[C:8]2[N:9]=[C:10](OS(C(F)(F)F)(=O)=O)[CH:11]=[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:7]=2[CH:6]=[N:5]1)([CH3:3])[CH3:2].[OH:26][CH2:27][C:28]1[CH:29]=[C:30](B(O)O)[CH:31]=[CH:32][CH:33]=1.C([O-])([O-])=O.[Na+].[Na+]>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>[OH:26][CH2:27][C:28]1[CH:33]=[C:32]([C:10]2[CH:11]=[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:7]3[CH:6]=[N:5][N:4]([CH:1]([CH3:3])[CH3:2])[C:8]=3[N:9]=2)[CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2734662[3-(Hydroxymethyl)phenyl]boronic acidHCID 86703405HCID 86703405, compound

Product 1

HCID 68295200HCID 68295200, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A solution of ethyl 1-isopropyl-6-(((trifluoromethyl)sulfonyl)oxy)-1H-pyrazolo[3,4-b]pyridine-4-carboxylate (1 g, 2.62 mmol), 3-(hydroxymethyl) phenyl boronic acid (0.438 g, 2.88 mmol) and Pd(PPh3)4 (0.303 g, 0.262 mmol) in 1,4-dioxane (15 mL) was purged with argon for 10 min. Then 2M Na2CO3 solution (4.5 mL, 9.4 mmol) was added to it and again argon was purged through it for 10 min. The reaction mixture was stirred at 100° C. for 1 h and after completion of the reaction water was added to it. Extraction was carried out using EtOAc the combined organic layers were washed with water dried over anhydrous Na2SO4; filtered and concentrated under reduced pressure. The residue was purified by column chromatography to give 0.81 g of target compound.

Workup

  1. customwas purged through it for 10 min
  2. customafter completion of the reaction water
  3. additionwas added to it
  4. extractionExtraction
  5. washwere washed with water
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by column chromatography
  10. customto give 0.81 g of target compound

Sources & evidence

ORD record
ord-05bf0f59b42d473790340a429d3c3550
Source dataset
uspto-grants-2013_12
Patent number
US08598167B1

Reaction notes

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