Potassium Phosphate, Tribasic → HCID 86725333, compound

HRID 925220Notes

Reaction equation

HRID 925220 reaction equation
[CH2:1]([O:4][C:5]([N:7]1[CH2:23][CH2:22][C:11]2[C:12]3[C:13]([CH3:21])([CH3:20])[CH2:14][CH2:15][C:16]=3[C:17](I)=[CH:18][C:10]=2[CH2:9][CH2:8]1)=[O:6])[CH2:2][CH3:3].[C:24]1(B(O)O)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C>C1COCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:1]([O:4][C:5]([N:7]1[CH2:23][CH2:22][C:11]2[C:12]3[C:13]([CH3:21])([CH3:20])[CH2:14][CH2:15][C:16]=3[C:17]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:18][C:10]=2[CH2:9][CH2:8]1)=[O:6])[CH2:2][CH3:3]

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 66827Phenylboronic AcidHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 86725334HCID 86725334, compound

Product 1

HCID 86725333HCID 86725333, compoundYield 46.9%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
120 °C

Procedure

Into a glass microwave vial, the product from step (a) (166 mg, 0.401 mmol), phenyl boronic acid (59 mg, 0.482 mmol), potassium phosphate tribasic (170 mg, 0.802 mmol), palladium acetate (9 mg, 0.040 mmol), and XPhos (38 mg, 0.080 mmol) in THF (2 ml) were added. The reaction mixture was heated in the microwave to 120° C. for 12 hours and then allowed to cool to room temperature. The mixture was filtered through celite and the filtrate was partitioned between saturated aqueous NaHCO3 and EtOAc. The aqueous layer was extracted with EtOAc (3×). The combined EtOAc extracts were washed with brine, dried over Na2SO4, and solvent evaporated in vacuo to give the crude product. Purification by silica-gel chromatography (gradient elution: 0-20%, EtOAc in hexanes) gave the sub-title compound as a white semi-solid (71 mg). 1H NMR (300 MHz, CDCl3) δ 7.41-7.39 (m, 4H); 7.33-7.30 (m, 1H); 7.00 (s, 1H); 4.17 (q, J=6.9 Hz, 2H); 3.67-3.61 (m, 4H); 3.08-3.05 (m, 2H); 2.95-2.93 (m, 2H); 2.84 (t, J=7.2 Hz, 2H); 1.88 (t, J=7.5 Hz, 2H); 1.40 (s, 6H); 1.27 (t, J=6.9 Hz, 3H); MS: ESI (positive): 400 (M+H).

Workup

  1. temperatureto cool to room temperature
  2. filtrationThe mixture was filtered through celite
  3. customthe filtrate was partitioned between saturated aqueous NaHCO3 and EtOAc
  4. extractionThe aqueous layer was extracted with EtOAc (3×)
  5. washThe combined EtOAc extracts were washed with brine
  6. dry with materialdried over Na2SO4, and solvent
  7. customevaporated in vacuo
  8. customto give the crude product
  9. customPurification
  10. washby silica-gel chromatography (gradient elution: 0-20%, EtOAc in hexanes)

Sources & evidence

ORD record
ord-b17ff5cc9a9b4674b8171c02b316ba78
Source dataset
uspto-grants-2016_03
Patent number
US09284277B2

Reaction notes

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