Potassium Phosphate, Tribasic → HCID 67168968, compound

HRID 2040336Notes

Reaction equation

HRID 2040336 reaction equation
Br[C:2]1[CH:3]=[C:4]([S:16]([NH2:19])(=[O:18])=[O:17])[CH:5]=[N:6][C:7]=1[NH:8][CH2:9][CH:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1.[CH2:20]([O:22]/[CH:23]=[CH:24]/B1OC(C)(C)C(C)(C)O1)[CH3:21].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CC#N.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:23]([O:22]/[CH:20]=[CH:21]/[C:2]1[CH:3]=[C:4]([S:16]([NH2:19])(=[O:18])=[O:17])[CH:5]=[N:6][C:7]=1[NH:8][CH2:9][CH:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1)[CH3:24]

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 219739081-Ethoxyethene-2-boronic acid pinacol esterHCID 67126423HCID 67126423, compound

Product 1

HCID 67168968HCID 67168968, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of EXAMPLE 388A (0.65 g), (E)-2-(2-ethoxyvinyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.735 g), palladium acetate (0.013 g), dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (0.057 g), and potassium phosphate (0.788 g) in CH3CN (9 ml) and water (6 mL) was heated at reflux overnight. After it cooled to room temperature, the reaction mixture was partitioned between water and ethyl acetate. The aqueous layer was extracted with additional ethyl acetate three times. The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica to give the title compound.

Workup

  1. temperatureat reflux overnight
  2. customthe reaction mixture was partitioned between water and ethyl acetate
  3. extractionThe aqueous layer was extracted with additional ethyl acetate three times
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by flash column chromatography on silica

Sources & evidence

ORD record
ord-4370eb5c1dd8416eb69be0e627d99915
Source dataset
uspto-grants-2013_11
Patent number
US08580794B2

Reaction notes

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