Phenylboronic Acid → HCID 66718401, compound

HRID 877007Notes

Reaction equation

HRID 877007 reaction equation
[NH2:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[N:10]=[N:9][N:8]([CH2:11][C:12]3[N:17]=[C:16]([N:18]4[CH2:22][CH2:21][CH2:20][C:19]4=[O:23])[CH:15]=[CH:14][CH:13]=3)[C:6]=2[N:7]=1.[C:25]1(B(O)O)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(=O)([O-])O.[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>[NH2:1][C:2]1[N:3]=[C:4]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:5]2[N:10]=[N:9][N:8]([CH2:11][C:12]3[N:17]=[C:16]([N:18]4[CH2:22][CH2:21][CH2:20][C:19]4=[O:23])[CH:15]=[CH:14][CH:13]=3)[C:6]=2[N:7]=1

Participants

6

Reactant 2

HCID 66827Phenylboronic AcidHCID 86655330HCID 86655330, compound

Product 1

HCID 66718401HCID 66718401, compoundYield 178.5%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of 1-[6-(5-amino-7-chloro[1,2,3]triazolo[4,5-d]pyrimidin-3-ylmethyl)pyridin-2-yl]pyrrolidin-2-one (0.50 g, 1.45 mmol) and phenylboronic acid (0.354 g, 2.90 mmol) in saturated aqueous sodium hydrogen carbonate (5 mL) and 1,4-dioxane (20 mL) was degassed with a stream of nitrogen for 10 min then treated with tetrakis(triphenylphosphine)palladium(0) (0.083 g, 0.0725 mmol), refluxed for 2 h then partitioned between EtOAc and water. The organic phase was separated and the aqueous phase re-extracted with EtOAc (×2). The combined organic extracts were dried (MgSO4), concentrated in vacuo to give a yellow solid (1.00 g) which was purified by column chromatography [SiO2; EtOAc-hexane (1:1) then EtOAc]. The resulting yellow solid (0.68 g) was triturated with diethyl ether to give the title compound (0.38 g, 68%) as an off-white solid.

Workup

  1. customwas degassed with a stream of nitrogen for 10 min
  2. temperaturerefluxed for 2 h
  3. customthen partitioned between EtOAc and water
  4. customThe organic phase was separated
  5. extractionthe aqueous phase re-extracted with EtOAc (×2)
  6. dry with materialThe combined organic extracts were dried (MgSO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5a840ed8df7548068bcfb56077973a23
Source dataset
uspto-grants-2015_03
Patent number
US08987279B2

Reaction notes

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