Potassium Phosphate, Tribasic → HCID 67960636, compound

HRID 1023583Notes

Reaction equation

HRID 1023583 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, compound2×

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 (Intermediate 122, 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-e62a167e91a546e7a59993e48147ecb9
Source dataset
uspto-grants-2014_05
Patent number
US08722695B2

Reaction notes

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