Potassium Phosphate, Tribasic → HCID 67960636, compound

HRID 527728Notes

Reaction equation

HRID 527728 reaction equation
[CH:1]1(B(O)O)[CH2:3][CH2:2]1.P(C1CCCCC1)(C1CCCCC1)C1CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].Br[C:35]1[CH:36]=[C:37]([CH:40]=[CH:41][C:42]=1[O:43][C:44]1[CH:49]=[CH:48][C:47]([N+:50]([O-:52])=[O:51])=[CH:46][N:45]=1)[C:38]#[N:39]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH:1]1([C:41]2[CH:40]=[C:37]([CH:36]=[CH:35][C:42]=2[O:43][C:44]2[CH:49]=[CH:48][C:47]([N+:50]([O-:52])=[O:51])=[CH:46][N:45]=2)[C:38]#[N:39])[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 2760897Cyclopropylboronic acidHCID 67235185HCID 67235185, compound

Product 1

HCID 67960636HCID 67960636, compoundYield 90.2%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

In a vial 3-bromo-4-[(5-nitro-2-pyridinyl)oxy]benzonitrile (Reference Intermediate R14, 800 mg) was dissolved in 16.0 mL of toluene. Cyclopropylboronic acid (1073.8 mg, 12.5 mmol) was added, followed by Pd(OAc)2 (56.1 mg, 0.25 mmol) and (Cy)3P (70.0 mg 0.25 mmol). Then, an aqueous solution (8.0 mL of water) of K3PO4 (1855.0 mg, 8.75 mmol) was added. The reaction mixture was heated at 80° C. overnight. After cooling down to r.t., the mixture was partitioned between brine and EtOAc and the separated aqueous phase was extracted with EtOAc (three times). The collected organic were dried over Na2SO4, filtered and evaporated. The crude obtained was charged on a silica gel column and eluted with Cyclohexane/EtOAc (from 100:0 to 80:20 Cyclohexane/EtOAc) affording 634 mg of the title compound.

Workup

  1. temperatureAfter cooling down to r.t.
  2. customthe mixture was partitioned between brine and EtOAc
  3. extractionthe separated aqueous phase was extracted with EtOAc (three times)
  4. dry with materialThe collected organic were dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude obtained
  8. additionwas charged on a silica gel column
  9. washeluted with Cyclohexane/EtOAc (from 100:0 to 80:20 Cyclohexane/EtOAc)

Sources & evidence

ORD record
ord-65de9d34996540478860bc11c1ab22dc
Source dataset
uspto-grants-2016_05
Patent number
US09346790B2

Reaction notes

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