Sodium Carbonate → HCID 59812138, compound

HRID 2114034Notes

Reaction equation

HRID 2114034 reaction equation
[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([C:19]4[CH:24]=[CH:23][C:22]([N:25]([CH3:27])[CH3:26])=[CH:21][CH:20]=4)[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:29]1[CH:33]=[CH:32][C:31](B(O)O)=[CH:30]1.C([O-])([O-])=O.[Na+].[Na+].[Li+].[Cl-]>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]4[CH:24]=[CH:23][C:22]([N:25]([CH3:27])[CH3:26])=[CH:21][CH:20]=4)[CH:18]=[C:13]3[C:12]([C:31]3[CH:32]=[CH:33][O:29][CH:30]=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 59811927HCID 59811927, compound

Product 1

HCID 59812138HCID 59812138, compoundYield 78%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

A mixture of 3 (300 mg, 0.596 mmol), EtOH (3.6 mL), toluene (3.6 mL), furan-3-boronic acid (100 mg, 0.894 mmol), 1M aq. Na2CO3 (1.49 mL, 1.49 mmol), LiCl (75.8 mg, 1.79 mmol) and PdCl2(PPh3)2 (41.8 mg, 59.6 μmol) was refluxed for 15 min. The organic layer was separated, brine was added, and the aqueous layer was extracted with AcOEt. The combined organic solutions were concentrated and separated by means of silicagel chromatography using hexane:AcOEt as eluent (in gradient up to 15% AcOEt) to give 4 as an orange foam (205 mg, 78%); 1H NMR (400 MHz, CDCl3) δ 3.03 (s, 6H), 6.73 (m, 1H), 6.84 (d, J=8.8 Hz, 2H), 7.45-7.65 (m, 6H), 7.84 (s, 2H), 8.05 (d, J=2.1 Hz, 1H), 8.26 (m, 2H), 8.68 (d, J=2.2 Hz, 1H).

Workup

  1. temperaturewas refluxed for 15 min
  2. customThe organic layer was separated
  3. additionbrine was added
  4. extractionthe aqueous layer was extracted with AcOEt
  5. concentrationThe combined organic solutions were concentrated
  6. customseparated by means of silicagel chromatography

Sources & evidence

ORD record
ord-2c211fd733904cef9de98ba77ae18bff
Source dataset
uspto-grants-2008_10
Patent number
US07432375B2

Reaction notes

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