Sodium Bicarbonate → HCID 66589882, compound

HRID 1092803Notes

Reaction equation

HRID 1092803 reaction equation
[CH:1]1([N:4]([CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[C:36]([Cl:40])[C:35]=2[Cl:41])[C:5]([C:7]2[C@@H:8]([CH2:28][O:29][CH2:30][O:31][CH3:32])[N:9]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:10][CH2:11][C:12]=2OS(C(F)(F)F)(=O)=O)=[O:6])[CH2:3][CH2:2]1.[OH:42][C:43]1[CH:48]=[CH:47][C:46](B(O)O)=[CH:45][CH:44]=1.C(=O)(O)[O-].[Na+]>O1CCOCC1>[CH:1]1([N:4]([CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[C:36]([Cl:40])[C:35]=2[Cl:41])[C:5]([C:7]2[C@@H:8]([CH2:28][O:29][CH2:30][O:31][CH3:32])[N:9]([C:21]([O:23][C:24]([CH3:26])([CH3:27])[CH3:25])=[O:22])[CH2:10][CH2:11][C:12]=2[C:46]2[CH:47]=[CH:48][C:43]([OH:42])=[CH:44][CH:45]=2)=[O:6])[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 27343604-Hydroxyphenylboronic acidHCID 86761501HCID 86761501, compound

Product 1

HCID 66589882HCID 66589882, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Into a 20 mL microwave vial was added 4G (1.33 g, 2.05 mmol) and 4-hydroxyphenyl boronic acid (425 mg, 3.1 mmol, 1.5 eq). Dioxane (12 mL) and saturated sodium bicarbonate (4 mL) was added and the mixture was degassed by bubbling N2 through the solution for 10 minutes. After degassing, 1,1′-bis-diphenyl phosphinoferrocene dichloro palladium (II) (Pd(dppf)Cl2) (150 mg, 206 μmol, 0.05 eq) was added and the reaction was capped. The reaction was microwaved at 150° C. for 20 minutes, and the reaction was transferred to a round bottom and the solvent was removed under vacuum. Saturated ammonium chloride (25 mL) and ethyl acetate (25 mL) was added to the residue and transferred to a separatory funnel. The organic layer was separated and the aqueous layer was further extracted with ethyl acetate (2×25 mL). The organic layers were combined and dried over sodium sulfate. Solution was filtered and the solvent was removed under vacuum. The residue was purified by column chromatography (40% ethyl acetate/hexanes) to give 4H (948 mg, 37%). ESI-MS:m/z 591.3 (M+H)+.

Workup

  1. customthe mixture was degassed
  2. customby bubbling N2 through the solution for 10 minutes
  3. customAfter degassing
  4. customthe reaction was capped
  5. customThe reaction was microwaved at 150° C. for 20 minutes
  6. customwas removed under vacuum
  7. additionSaturated ammonium chloride (25 mL) and ethyl acetate (25 mL) was added to the residue
  8. customtransferred to a separatory funnel
  9. customThe organic layer was separated
  10. extractionthe aqueous layer was further extracted with ethyl acetate (2×25 mL)
  11. dry with materialdried over sodium sulfate
  12. filtrationSolution was filtered
  13. customthe solvent was removed under vacuum
  14. customThe residue was purified by column chromatography (40% ethyl acetate/hexanes)
  15. customto give 4H (948 mg, 37%)

Sources & evidence

ORD record
ord-ab06c4bfd2e44fd7aab51c5bdac11fd6
Source dataset
uspto-grants-2012_03
Patent number
US08129538B1

Reaction notes

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