Potassium Phosphate, Tribasic → HCID 68775560, compound

HRID 2191085Notes

Reaction equation

HRID 2191085 reaction equation
Br[C:2]1[C:11]2[CH2:10][C:9]([CH3:13])([CH3:12])[CH2:8][NH:7][C:6](=[O:14])[C:5]=2[S:4][C:3]=1[N:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1.[C:21]1(B(O)O)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>CCOC(C)=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CN(C=O)C>[CH3:12][C:9]1([CH3:13])[CH2:8][NH:7][C:6](=[O:14])[C:5]2[S:4][C:3]([N:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[C:2]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:11]=2[CH2:10]1

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, Tribasic2×HCID 66827Phenylboronic Acid2×HCID 812191,3-Bis(diphenylphosphino)propane2×HCID 68774673HCID 68774673, compound

Product 1

HCID 68775560HCID 68775560, compoundYield 37%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalyst2×HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of Example 116 (0.15 g, 0.41 mmol), phenylboronic acid (0.08 g, 0.63 mmol), palladium acetate (0.005 g, 0.02 mmol), 1,3-bis(diphenylphosphino)propane (0.02 g, 0.04 mmol) and K3PO4 (0.18 g, 0.82 mmol) was added DMF (2 mL). The reaction mixture was heated at 80° C. for 5 h and left standing for 16 h at r.t. Phenyl-boronic acid (0.08 g, 0.63 mmol), palladium acetate (0.005 g, 0.02 mmol), 1,3-bis(diphenylphosphino)propane (0.02 g, 0.04 mmol), K3PO4 (0.07 g, 0.33 mmol) and DMF (2 mL) were again added. The reaction mixture was heated at 90° C. for 16 h, then cooled to r.t. and diluted with EtOAc (5 mL). The solid was filtered and washed with EtOAc (25 mL). The organic filtrate was washed with water (5×10 mL), then brine (10 mL), dried (Na2SO4), filtered and concentrated in vacuo. Purification by column chromatography (SiO2, 30% EtOAc/hexanes) gave the title compound (0.05 g, 37%) as a white solid. δH (DMSO-d6) 7.83 (1H, t, J 5.1 Hz), 7.46 (2H, t, J 7.4 Hz), 7.37-7.29 (3H, m), 3.49-3.47 (4H, m), 2.85 (2H, d, J 5.2 Hz), 2.79-2.77 (4H, m), 2.29 (2H, s), 0.86 (6H, s). MS (ES+) 357.0 (M+H)+.

Workup

  1. waitleft
  2. temperatureThe reaction mixture was heated at 90° C. for 16 h
  3. temperaturecooled to r.t.
  4. filtrationThe solid was filtered
  5. washwashed with EtOAc (25 mL)
  6. washThe organic filtrate was washed with water (5×10 mL)
  7. dry with materialbrine (10 mL), dried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customPurification by column chromatography (SiO2, 30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-3cd6427f0d19494f97296e542f6f6001
Source dataset
uspto-grants-2012_12
Patent number
US08324204B2

Reaction notes

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