Sodium Carbonate → HCID 59812080, compound

HRID 2114058Notes

Reaction equation

HRID 2114058 reaction equation
[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([C:19]#[N:20])[CH:18]=[C:13]3[C:12](I)=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:22]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23]1.[Li+].[Cl-].C([O-])([O-])=O.[Na+].[Na+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1(C)C=CC=CC=1.CCO>[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([C:19]#[N:20])[CH:18]=[C:13]3[C:12]([C:24]3[CH:25]=[CH:26][O:22][CH:23]=3)=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 2734358Furan-3-boronic acidHCID 59812105HCID 59812105, compound

Product 1

HCID 59812080HCID 59812080, compoundYield 72%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

A mixture of iodide 37 (2.00 g, 4.89 mmol), furan-3-boronic acid (820 mg, 7.33 mmol), PdCl2(PPh3)2 (343 mg, 0.49 mmol), LiCl (622 mg, 14.7 mmol), 1.0 M aqueous Na2CO3 (12.2 mL, 12.2 mmol), EtOH (23 mL) and toluene (23 mL) were refluxed for 50 min. After cooling the layers were separated, brine was added to the aqueous layer and extracted with ethyl acetate (3×50 mL). The combined organic extracts were dried (MgSO4) and concentrated. The resulting solid was purified by silicagel chromatography using 30% ethyl acetate in hexane (gradient elution) to give 38 as an orange solid (1.23 g, 72%);

Workup

  1. temperaturewere refluxed for 50 min
  2. temperatureAfter cooling the layers
  3. customwere separated
  4. additionbrine was added to the aqueous layer
  5. extractionextracted with ethyl acetate (3×50 mL)
  6. dry with materialThe combined organic extracts were dried (MgSO4)
  7. concentrationconcentrated
  8. customThe resulting solid was purified by silicagel chromatography

Sources & evidence

ORD record
ord-d749767704fb4bc98b76a32b2c811e97
Source dataset
uspto-grants-2008_10
Patent number
US07432375B2

Reaction notes

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