Potassium Phosphate, Tribasic → HCID 57567190, compound

HRID 1727295Notes

Reaction equation

HRID 1727295 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].Br[C:20]1[C:21](=[O:38])[O:22]/[C:23](=[CH:27]\[C:28]2[C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[CH:31]=[CH:30][CH:29]=2)/[C:24]=1[O:25][CH3:26].O1CCOCC1.C1COCC1>O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:20]2[C:21](=[O:38])[O:22]/[C:23](=[CH:27]\[C:28]3[C:37]4[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=4)[CH:31]=[CH:30][CH:29]=3)/[C:24]=2[O:25][CH3:26])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 742994-Chlorophenylboronic acidHCID 22018518Dioxane tetrahydrofuranHCID 57567186HCID 57567186, compound

Product 1

HCID 57567190HCID 57567190, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A stirred mixture of 4-chlorophenylboronic acid (259 mg, 166 mmol), K3PO4 (962 mg, 4.53 mmol) and Pd(PPh3)4 (52 mg, 45.3 μmol) under N2 is treated sequentially with of 3-bromo-4-methoxy-5[(Z)-1-naphthylmethylidene]furan-2(5H)-one (500 mg, 1.51 mmol) and 9.3 mL of a 2:1 v/v mixture of dioxane/THF, heated at 90° C. until the disappearance of starting material by thin layer chromatography, cooled to room temperature, diluted with water and extracted with EtOAc. The extracts are combined, dried over MgSO4 and concentrated in vacuo. The resultant residue is purified by flash chromatography (silica gel, 25% EtOAc in hexanes as eluent) to afford the title product as a yellow solid, 380 mg (69% yield), identified by NMR and mass spectral analyses.

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted with EtOAc
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe resultant residue is purified by flash chromatography (silica gel, 25% EtOAc in hexanes as eluent)

Sources & evidence

ORD record
ord-072d8a82e19641bda04caed13a40790b
Source dataset
uspto-grants-2009_02
Patent number
US07495027B2

Reaction notes

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