Sodium Bicarbonate → HCID 69000600, compound

HRID 1909707Notes

Reaction equation

HRID 1909707 reaction equation
I[C:2]1[CH:16]=[CH:15][C:5]([CH2:6][C:7]2[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.C([O-])(O)=O.[Na+].[S:22]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23]1.C1(C)C=CC=CC=1.CCO>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>[CH3:14][O:13][C:10]1[CH:11]=[CH:12][C:7]([CH2:6][C:5]2[CH:15]=[CH:16][C:2]([C:24]3[CH:25]=[CH:26][S:22][CH:23]=3)=[CH:3][CH:4]=2)=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 581760Thiophene-3-boronic acidHCID 21863594Toluene ethanolHCID 44819342HCID 44819342, compound

Product 1

HCID 69000600HCID 69000600, compoundYield 48.2%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Procedure

To a mixture of 1-(4-iodobenzyl)-4-methoxybenzene (0.300 g, 0.925 mmol), 2N aqueous NaHCO3 solution (1.85 mL, 3.7 mmol), and 3-thiopheneboronic acid (0.237 g, 1.85 mmol) in a solution of toluene/EtOH (17.6/0.8 mL) at ambient temperature under an atmosphere of nitrogen was added tetrakis(triphenylphosphine)palladium(0) (0.107 g, 0.093 mmol). The mixture was refluxed for 18 h, cooled to ambient temperature, and diluted with H2O (30 mL). After extracting with EtOAc (3×25 mL) and filtering the EtOAc through a silica gel bed, the organic layer was washed with brine (25 mL), dried over anhydrous sodium sulfate, concentrated in vacuo, and purified by flash column chromatography (70% hexane in dichloromethane) to afford the title product as a white solid (0.125 g, 48%): 1H NMR (400 MHz, CDCl3): δ 7.50 (d, 2H, J=8.4 Hz), 7.40 (t, 1H, J=2.0 Hz), 7.36 (d, 2H, J=2.4 Hz), 7.20 (d, 2H, J=8.4 Hz), 7.12 (d, 2H, J=8.8 Hz), 6.84 (d, 2H, J=8.8 Hz), 3.94 (s, 2H), 3.78 (s, 3H).

Workup

  1. temperatureThe mixture was refluxed for 18 h
  2. extractionAfter extracting with EtOAc (3×25 mL)
  3. filtrationfiltering the EtOAc through a silica gel bed
  4. washthe organic layer was washed with brine (25 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. custompurified by flash column chromatography (70% hexane in dichloromethane)

Sources & evidence

ORD record
ord-580bcbdbed9c4580b000d2b8f8896449
Source dataset
uspto-grants-2013_12
Patent number
US08598359B2

Reaction notes

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