Potassium Phosphate, Tribasic → HCID 67126809, compound

HRID 574880Notes

Reaction equation

HRID 574880 reaction equation
[OH:1][C:2]1([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2OS(C(F)(F)F)(=O)=O)[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[Cl:30][C:31]1[CH:36]=[CH:35][C:34](B(O)O)=[CH:33][CH:32]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>CC1CCCO1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Cl:30][C:31]1[CH:36]=[CH:35][C:34]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[CH2:15][C:2]2([OH:1])[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:9])[CH2:4][CH2:3]2)=[CH:33][CH:32]=1

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 742994-Chlorophenylboronic acidHCID 87279446HCID 87279446, compound

Product 1

HCID 67126809HCID 67126809, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 73012-MethyltetrahydrofuranSolvent

Procedure

A mixture of EXAMPLE 263D (4.3 g), 4-chlorophenylboronic acid (1.84 g), K3PO4 (2.91 g), and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.36 g) in 2-methyltetrahydrofuran (50 mL) was stirred at 70° C. for 24 hours. The reaction was cooled and quenched with water (50 mL), extracted twice with ether, and the combined extracts were washed with brine, dried over Na2SO4, filtered, and concentrated. The crude product was chromatographed on silica gel using 5-30% ethyl acetate in hexanes to provide the title compound.

Workup

  1. temperatureThe reaction was cooled
  2. customquenched with water (50 mL)
  3. extractionextracted twice with ether
  4. washthe combined extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was chromatographed on silica gel using 5-30% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-7148cc31c0a340debcdfe3a1ea8c12e0
Source dataset
uspto-grants-2015_05
Patent number
US09034875B2

Reaction notes

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