Sodium Carbonate → HCID 90384207, compound

HRID 928649Notes

Reaction equation

HRID 928649 reaction equation
Br[C:2]1[C:10]2[O:9][CH:8]=[CH:7][C:6]=2[CH:5]=[C:4]([F:11])[CH:3]=1.[OH:12][C:13]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+].O1CCOCC1>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].O>[F:11][C:4]1[CH:3]=[C:2]([C:16]2[CH:17]=[CH:18][C:13]([OH:12])=[CH:14][CH:15]=2)[C:10]2[O:9][CH:8]=[CH:7][C:6]=2[CH:5]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 27343604-Hydroxyphenylboronic acidHCID 221448167-Bromo-5-fluoro-1-benzofuran

Product 1

HCID 90384207HCID 90384207, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To the compound (210 mg, 0.977 mmol) of Step 1, 4-hydroxyphenylboronic acid (162 mg, 1.17 mmol), sodium carbonate (228 mg, 2.15 mmol), and Pd(dppf)Cl2 (catalytic amount), 1,4-dioxane (1.2 mL) and water (0.4 mL) were added, and stirred at 100° C. for 2 hours. The reaction solution was concentrated under reduced pressure. To the residue, ethyl acetate and 1 N hydrochloric acid were added and stirred. After that, the insoluble material was filtered off, and extraction was performed with ethyl acetate. The organic phase was washed with saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was distilled away under reduced pressure. The resulting residue was purified by silica gel chromatography (hexane/ethyl acetate) to thus obtain the title compound.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. additionTo the residue, ethyl acetate and 1 N hydrochloric acid were added
  3. stirringstirred
  4. filtrationAfter that, the insoluble material was filtered off
  5. extractionextraction
  6. washThe organic phase was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationThe solvent was distilled away under reduced pressure
  9. customThe resulting residue was purified by silica gel chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-8a39641bd5ee416b9f89aace09422eb7
Source dataset
uspto-grants-2016_03
Patent number
US09290487B2

Reaction notes

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