Hydrochloric Acid → HCID 86646394, compound

HRID 1877240Notes

Reaction equation

HRID 1877240 reaction equation
Br[C:2]1[S:6][C:5]([CH3:7])=[C:4]([CH:8]2[O:12]CCO2)[CH:3]=1.[F:13][C:14]([F:25])([F:24])[C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1.C(=O)([O-])[O-].[Na+].[Na+].P([O-])([O-])([O-])=O.Cl>O1CCCC1.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].ClCCl.CN(C)C=O.O>[CH3:7][C:5]1[S:6][C:2]([C:18]2[CH:19]=[CH:20][C:15]([C:14]([F:25])([F:24])[F:13])=[CH:16][CH:17]=2)=[CH:3][C:4]=1[CH:8]=[O:12]

Participants

11

Reactant 5

HCID 313Hydrochloric AcidHCID 1061PhosphateHCID 10340Sodium CarbonateHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 68516498HCID 68516498, compound

Product 1

HCID 86646394HCID 86646394, compoundYield 66.1%

Reagents, catalysts & solvents 5

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 2-(5-bromo-2-methylthiophen-3-yl)-1,3-dioxolane (3.25 g) synthesized in Example 278 (3), 4-(trifluoromethyl)phenylboronic acid (3.70 g), sodium carbonate (2.76 g), water (10 mL) and N,N-dimethylformamide (50 mL) was added [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II).dichloromethane adduct (1.06 g). The reaction mixture was deaerated and stirred at 80° C. for 4 hr under an argon atmosphere. Phosphate buffer was added to quench the reaction, and the mixture was extracted with ethyl acetate. The extract was washed with saturated sodium hydrogen carbonate and saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (20% ethyl acetate/hexane) to give a pale-yellow solid. To a solution of the obtained solid in tetrahydrofuran (25 mL) was added 1N hydrochloric acid (10 mL), and the mixture was stirred at room temperature for 1 hr. Tetrahydrofuran was evaporated using evaporator, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate and concentrated under reduced pressure to give the title compound (2.33 g, 66%) as a white solid.

Workup

  1. customto quench
  2. customthe reaction
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated sodium hydrogen carbonate and saturated brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (20% ethyl acetate/hexane)
  8. customto give a pale-yellow solid
  9. stirringthe mixture was stirred at room temperature for 1 hr
  10. customTetrahydrofuran was evaporated
  11. customevaporator
  12. extractionthe mixture was extracted with ethyl acetate
  13. washThe extract was washed with saturated brine
  14. dry with materialdried over magnesium sulfate
  15. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9bc6aa955af44cf6ad2e1281ba830735
Source dataset
uspto-grants-2012_11
Patent number
US08309580B2

Reaction notes

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